[ CAS No. 3364-80-5 ]

Name: 3364-80-5|Thiazole-4-carbaldehyde|97%
Brand: Ambeed
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Product Details of [ 3364-80-5 ]

CAS No. :	3364-80-5	MDL No. :	MFCD00626896
Formula :	C₄H₃NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WRFKSVINLIQRKF-UHFFFAOYSA-N
M.W :	113.14 g/mol	Pubchem ID :	2763214
Synonyms :

Calculated chemistry of [ 3364-80-5 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	27.5
TPSA :	58.2 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.8
Log Po/w (XLOGP3) :	0.75
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	-0.97
Log Po/w (SILICOS-IT) :	2.32
Consensus Log Po/w :	0.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.48
Solubility :	3.78 mg/ml ; 0.0334 mol/l
Class :	Very soluble
Log S (Ali) :	-1.55
Solubility :	3.18 mg/ml ; 0.0281 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.18
Solubility :	7.41 mg/ml ; 0.0655 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 3364-80-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3364-80-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3364-80-5 ]
Downstream synthetic route of [ 3364-80-5 ]

[ 3364-80-5 ] Synthesis Path-Upstream 1~10

1
[ 936371-70-9 ]
[ 3364-80-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1850 - 1864

2
[ 3364-76-9 ]
[ 3364-80-5 ]

Reference： [1] Patent: WO2004/60889, 2004, A1, . Location in patent: Page 20

3
[ 3364-79-2 ]
[ 3364-80-5 ]

Reference： [1] Heterocycles, 2004, vol. 63, # 10, p. 2385 - 2392

4
[ 116045-55-7 ]
[ 3364-80-5 ]

Reference： [1] Synthesis, 1987, # 11, p. 998 - 1001

5
[ 99185-90-7 ]
[ 3364-80-5 ]

Reference： [1] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
[2] Helvetica Chimica Acta, 1951, vol. 34, p. 143,147

6
[ 41040-93-1 ]
[ 3364-80-5 ]

Reference： [1] Journal of Organic Chemistry, 1973, vol. 38, p. 3316 - 3318
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1265 - 1268

7
[ 41040-93-1 ]
[ 3364-80-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1265 - 1268

8
[ 3364-80-5 ]
[ 7036-04-6 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	at 0℃; for 1 h;	To a solution of thiazole-4-carboxaldehyde (0.810 ml, 9.67 mmol, Combi-Blocks Inc.) in MeOH (48.3 ml) at 0 °C was added sodium borohydride (0.341 ml, 9.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in portions. The reaction mixture was allowed to stir for 1 hour. Saturated aqueous ammonium chloride solution was carefully added and the reaction mixture was filtered. The filtrate was concentrated in vacuo. The solid was taken up in 10percent MeOH/DCM and filtered through a plug of silica gel to provide thiazol- 4-ylmethanol (0.826 g, 7.18 mmol, 74.3percent yield) as a yellow oil. MS m/z = 116.0 [M+H]⁺. Calculated for C₄H₅NOS: 115.009. H NMR (400 MHz, CHLOROFORM -J) δ ppm 2.58 (br. s., 1 H) 4.86 (s, 2 H) 7.27 - 7.30 (m, 1 H) 8.83 (d, J=l .76 Hz, 1 H)

Reference： [1] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 167; 168
[2] Patent: WO2010/132999, 2010, A1, . Location in patent: Page/Page column 137

9
[ 3364-80-5 ]
[ 1452-15-9 ]

Reference： [1] Synlett, 2009, # 20, p. 3378 - 3382

10
[ 3364-80-5 ]
[ 95-54-5 ]
[ 148-79-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium metabisulfite In N,N-dimethyl-formamide at 120℃;	General procedure: A solution of substituted o-phenyldiamine (1.0 equiv), thiazole-4-aldehyde or pyridine-2-aldehyde (1.0 equiv) with sodium pyrosulfite in DMF was stirred at 120° C overnight. On completion of the reaction monitored by TLC, the solvent was evaporated and the residue was purified by silica gel chromatography by DCM/MeOH system to afford the final product. If necessary, the crudeproduct could be recrystallized in DCM or dichloroethane to afford pure sample.

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3774 - 3780
[2] Journal of the American Chemical Society, [3] Journal of the American Chemical Society, 2010, vol. 132, p. 1230 - 1231
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1985 - 1988
[5] Molecules, 2017, vol. 22, # 2,
[6] Patent: US10125116, 2018, B2, . Location in patent: Page/Page column 6

[ 3364-80-5 ] Synthesis Path-Downstream 1~59

1
[ 41040-93-1 ]
[ 3364-80-5 ]

Reference： [1]Journal of Organic Chemistry,1973,vol. 38,p. 3316 - 3318
[2]Journal of the Chemical Society. Perkin transactions II,1986,p. 1265 - 1268

2
[ 3364-80-5 ]
[ 79265-30-8 ]
[ 112969-98-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1748 - 1761

3
[ 3364-80-5 ]
[ 35198-67-5 ]
[ 26097-80-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 539 - 541

4
[ 3364-80-5 ]
[ 136609-85-3 ]
5-methyl-6-<2-(4-thiazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 129 - 140

5
[ 3364-80-5 ]
[ 41827-98-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 2321 - 2330
[2]Synthesis,1987,p. 998 - 1001
[3]Organic Letters,2015,vol. 17,p. 4542 - 4545

6
[ 116045-55-7 ]
[ 3364-80-5 ]

Reference： [1]Synthesis,1987,p. 998 - 1001

7
[ 936371-70-9 ]
[ 3364-80-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1850 - 1864

8
[ 3364-80-5 ]
[ 3453-00-7 ]
[ 936331-91-8 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1875 - 1878

9
[ 3364-76-9 ]
[ 3364-80-5 ]

Yield	Reaction Conditions	Operation in experiment
		A stirred mixture of 4-CHLOROMETHYLTHIAZOLE (1g, 5.88 MMOL) and hexamine (1.64g, 11.76 mmol, 2eq) in 50percent acetic acid (10 mL) was heated at reflux for 3 hours. The reaction mixture was allowed to cool for five minutes and then concentrated hydrochloric acid (2.5 mL) was added. The resulting reaction mixture was refluxed for a further five minutes prior to dilution of the reaction mixture with water (50 mL). The resulting reaction mixture was extracted with dichloromethane (6 x 50 mL). The extracts were combined and washed once with sodium bicarbonate (50 mL), dried over NA2SO4 AND evaporated to give the title compound as a gum. 'H NMR (CDCI3) : 8 10. 14 (s, 1H), 8.93 (s, 1H), 8.28 (s, 1H).

Reference： [1]Patent: WO2004/60889,2004,A1 .Location in patent: Page 20

10
[ 3364-80-5 ]
leucine tert-butyl ester hydrochloride [ No CAS ]
[ 521956-39-8 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 1, 3-thiazole-4-carboxaldehyde (Synthesis, 1987, 998; 1.97 g, 17.5 MMOL) and 2-amino-4-methylpentanoic acid TERT-BUTYL ester, hydrochloride (3.91 g, 17.5 MMOL) in a similar manner to that described for Intermediate 1.
	With triethylamine; In dichloromethane; for 20h;Heating / reflux;	A stirred mixture of 2-amino-4-methyl-pentanoic acid tert-butyl ester, hydrochloride (2. 1G, 9.38 mmol), 1, 3-thiazole-4-carboxaldehyde (Intermediate b) (1. 06 g, 9.38 MMOL) and triethylamine (1.31 mL, 9.38 MMOL) in dichloromethane (25 mL) was heated under reflux under nitrogen for 20 hours. The reaction mixture was allowed to cool to room temperature, washed twice with water, dried over NA2SO4 and evaporated to give the title compound as an oil. 'H NMR (CDCI3) : 5 8.84 (s, 1H), 8.49 (d, 1 H), 8.01 (s, 1H), 4.00 (dd, 1 H), 1.90-1. 70 (m, 2H), 1.64-1. 56 (m, 1H), 1.47 (s, 9H), 0.96 (d, 3H) and 0.91 (d, 3H).

Reference： [1]Patent: WO2004/60889,2004,A1 .Location in patent: Page 15
[2]Patent: WO2004/60889,2004,A1 .Location in patent: Page 20

11
[ 3364-80-5 ]
2-Hydroxy-2-(thiazol-4-yl)ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With sodium borohydrid; trifluoroacetic acid; In tetrahydrofuran;	EXAMPLE Q 2-Hydroxy-2-(thiazol-4-yl)ethanamine Prepared analogously to Example P by reaction of 4-formyl-thiazole with sodium borohydride and trifluoroacetic acid in tetrahydrofuran. The product obtained by extraction with methylene chloride is purified on a silica gel column using methanol as eluant. Yield: 19percent of theory 1 H-NMR spectrum (CDCl3 /CD3 OD): delta=4.880 ppm (dd, =CHOH)

Reference： [1]Patent: US4886814,1989,A

12
[ 3364-80-5 ]
[ 1018987-99-9 ]
[ 1018988-00-5 ]

Yield	Reaction Conditions	Operation in experiment
49%		Compound 1C (3.3 g, 8.3 mmol) and <strong>[3364-80-5]4-thiazolecarboxaldehyde</strong> (1.4 g, 12.4 mmol) in dichloroethane (16 mL) were stirred for 30 min. under nitrogen. Sodium triacetoxyborohydride (5.3 g, 24.9 mmol) was added and the reaction was stirred for 20 h. The mixture was diluted with CH2CI2 (20 mL) and washed with saturated aqueous NaHCO3. The organic phase was dried over Na2SO4 and concentrated. Column chromatography (12O g silica gel, eluting with 4percent 7N NH3/MeOH in CH2Cl2) gave 2.01 g ID as a white solid (49percent). 1H NMR (500.333 MHz, CDC13) delta 8.90 (dd, J= 4.1, 1.7 Hz, IH), 8.76 (d, J= 1.9 Hz, IH), 8.11 (dd, J= 8.0, 1.5 Hz, IH), 7.72 (dd, J = 7.3, 2.3 Hz, IH), 7.51-7.46 (m, 2H), 7.37-7.33 (m, 3H), 7.31-7.29 (m, 2H), 7.18 (s, IH), 3.85 (s, br, 2H), 3.76 (s, 2H), 3.67 (br s, 2H), 3.26 (br s, IH), 3.02 (s, 3H), 2.78-2.71 (m, IH), 2.67-2.52 (m, 4H), 2.46-2.37 (m, IH), 2.14-2.04 (m, 2H). TOF MS E+ 499.21.

Reference： [1]Patent: WO2008/48171,2008,A1 .Location in patent: Page/Page column 25

13
[ 3364-80-5 ]
[ 10272-07-8 ]
[ 1092389-48-4 ]

Reference： [1]Synlett,2008,p. 2429 - 2432

14
[ 3364-80-5 ]
[ 873692-91-2 ]
[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 14; To a cooled (-78° C.) solution of [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (200 mg, 0.7 mmol) in anhydrous toluene (8 mL), TMEDA (110 uL, 0.7 mmol) was added followed by nBuLi (0.47 mL, 0.75 mmol, 1.6M in hexanes). The mixture was stirred for 40 min at -78° C. and a solution of <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (0.32 g, 2.8 mmol) in dichloromethane (1 mL) was added. The mixture was stirred for 16 hrs during which the temperature reached room temperature. The reaction was quenched with water, the resulting mixture was basified by the addition of NH4OH and extracted with EtOAc. The combined organic layers were concentrated and subjected to mass triggered preparative HPLC to afford [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanol (Compound 14-1) (200 mg). MH+=318.8.

Reference： [1]Patent: US2006/14797,2006,A1 .Location in patent: Page/Page column 26

15
[ 3364-80-5 ]
[ 911491-26-4 ]
[ 911491-65-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4245 - 4249

16
[ 3364-80-5 ]
[ 1018678-55-1 ]
C₂₀H₁₇F₃N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4555 - 4559

17
[ 3364-80-5 ]
[ 1018678-63-1 ]
C₁₉H₁₅F₃N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4555 - 4559

18
[ 3364-80-5 ]
[ 95-54-5 ]
[ 148-79-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium metabisulfite; In N,N-dimethyl-formamide; at 120℃;	General procedure: A solution of substituted o-phenyldiamine (1.0 equiv), thiazole-4-aldehyde or pyridine-2-aldehyde (1.0 equiv) with sodium pyrosulfite in DMF was stirred at 120° C overnight. On completion of the reaction monitored by TLC, the solvent was evaporated and the residue was purified by silica gel chromatography by DCM/MeOH system to afford the final product. If necessary, the crudeproduct could be recrystallized in DCM or dichloroethane to afford pure sample.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3774 - 3780
[2]Journal of the American Chemical Society,2010,vol. 132,p. 1230 - 1231
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1985 - 1988
[4]Molecules,2017,vol. 22
[5]Patent: US10125116,2018,B2 .Location in patent: Page/Page column 6

19
[ 3364-80-5 ]
[ 73874-95-0 ]
[ 1228837-31-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

20
[ 3364-80-5 ]
[ 7524-50-7 ]
[ 1240523-18-5 ]

Yield	Reaction Conditions	Operation in experiment
		(S)-Methyl 3-phenyl-2-(thiazol-4-ylmethylamino)propanoate (34.8.C).L-Phenylalanine methyl ester HCl 34.8.A (2.15 g, 10.0 mmol) was partitioned with DCM and saturated NaHCO3. The aqueous layer was extracted with DCM (2X). The organic layers were combined, dried with sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM (30 ml) and AcOH (571 muL, 10 mmol), thiazole-4-carboxaldehyde 34.8.B (1.13 g, 10 mmol), and NaBH(OAc)3 (4.24 g, 20 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with NaHCO3(sat) and extracted with DCM. The organic extracts were dried with sodium sulfate, filtered, and concentrated. The resulting residue was partially purified on a silica gel column (120 g, 0-8percent MeOH:DCM) to yield 34.8.C as a crude oil (2.25 g).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 114-115

21
[ 3364-80-5 ]
[ 1240521-67-8 ]
[ 1240521-68-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 25℃;	(2S)-3-(4-fluorophenyl)-N-(l-methyl-3-(2-(methylamino)pyrimidin-4-yl)- lH-pyrazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide (9). The reaction mixture of (2iS)-2-amino-3 -(4-fluorophenyl)-N-( 1 -methyl-3 -(2-(methylamino)pyrimidin-4-yl)- 1 H- pyrazol-5-yl)propanamide, 9.F (20.0 mg, 54.0 mumol), <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (7.4 mg, 65.0 mumol) and sodium triacetoxyborohydride (34.0 mg, 162.0 mumol) in DCE (1.0 ml), DMF (0.1 ml) and sodium acetate (3eqv. 3.0 mg) was stirred at 25 0C overnight. The LCMS indicated compound 9 was formed. The crude mixture was purified by preperative HPLC to give the compound 9. 1H NMR (500 MHz, MeOH) delta ppm 9.13 (1 H, d, J= 2.0 Hz), 8.23 (1 H, d, J= 5.0 Hz), 7.82 (1 H, s), 7.35 (1 H, d, J = 5.0 Hz). 7.32-7.30 (2 H, m), 7.13-7.11 (2 H, m), 6.95 (1 H, s), 4.53-4.46 (2 H, m), 4.37-4.34 (1 H, m), 3.62 (3 H, s), 3.46-3.45(1 H, m), 3.23-3.21(1 H, m), 3.08 (3 H, s). MS ESI (pos.) m/e: 467.2 (M+H)+.

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 55

22
[ 3364-80-5 ]
[ 1240521-75-8 ]
[ 1240521-76-9 ]

Yield	Reaction Conditions	Operation in experiment
25%		(2S)-N-(3-(lH-pyrazol-3-yl)phenyl)-3-phenyl-2-(thiazol-4- ylmethylamino)propanamide (12). To a solution of (2S)-N-(3-(lH-pyrazol-3-yl)phenyl)-2- amino-3-phenylpropanamide 12.C (200 mg, 0.65 mmol) in DCM (5 mL) was added thiazole- 4-carbaldehyde (73 mg, 0.65 mmol, available from Combi-Blocks). The mixture was stirred for Ih, then sodium triacetoxyborohydride (207mg, 0.98mmol) was added and the mixture stirred for an additional hour at room temperature. The mixture was then concentrated and the crude product purified by reverse phase chromatography (0-100percent CH3CN/water + 0.5percent TFA) to afford (2S)-N-(3-(lH-pyrazol-3-yl)phenyl)-3-phenyl-2-(thiazol-4- ylmethylamino)propanamide 12 as a white solid (66.7 mg, 25percent yield). LCMS ESI (pos.) m/e: 404.0 (M+l): IH NMR (500 MHz, MeOH-D4) delta ppm 9.11 (d, J=I .96 Hz, 1 H), 7.82 - 7.87 (m, 1 H), 7.80 (d, J=I.96 Hz, 1 H), 7.74 (d, J=2.20 Hz, 1 H), 7.51 - 7.60 (m, 1 H), 7.21 - 7.38 (m, 7 H), 6.68 (d, J=2.20 Hz, 1 H), 4.50 (d, J=5.38 Hz, 2 H), 4.29 (dd, J=9.29, 5.87 Hz, 1 H), 3.43 (dd, J=13.45, 5.62 Hz, 1 H), 3.27 (dd, J=13.45, 9.29 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 59-60

23
[ 3364-80-5 ]
[ 1240521-91-8 ]
[ 1240521-92-9 ]
(2S)-N-(2-methoxy-5-(1H-pyrazol-4-yl)pyridin-3-yl)-3-phenyl-2-(thiazol-5-ylmethylamino)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		(2S)-N-(2-methoxy-5-(lH-pyrazol-4-yl)pyridin-3-yl)-3-phenyl-2-(thiazol-5- ylmethylamino)propanamide (15.1). To a solution of a 1 :9 mixture of (2S)-2-amino-N-(2- methoxy-5-(lH-pyrazol-4-yl)pyridin-3-yl)-3-phenylpropanamide 15.1. D and (S)-2-amino-N- (2-oxo-5-(lH-pyrazol-4-yl)-l,2-dihydropyridin-3-yl)-3-phenylpropanamide (90 mg, 0.28 mmol) in DCM (1 rnL) was added <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (26 mg, 0.28 mmol) and was then stirred for 1 hour. Sodium triacetoxyborohydride (170 mg, 0.82 mmol) and acetic acid (16 muL, 0.28 mmol) was then added, the mixture was stirred for an additional 1 hour at room temperature, concentrated and the crude product purified by reverse phase chromatography (0-100percent CH3CN/water + 0.5percent TFA) to afford (2S)-N-(2-methoxy-5-(lH-pyrazol-4- yl)pyridin-3-yl)-3-phenyl-2-(thiazol-5-ylmethylamino)propanamide 15.1 (5.7 mg, 57percent) as a white solid. LCMS ESI (pos.) m/e: 435.1 (M+l): IH NMR (500 MHz, MeOH-D4) delta ppm 9.13 (d, J=I.83 Hz, 1 H), 8.50 (d, J=I.83 Hz, 1 H), 8.15 (d, J=I.83 Hz, 1 H), 7.94 (s, 2 H), 7.80 (d, J=I.83 Hz, 1 H), 7.25 - 7.39 (m, 5 H), 4.46 - 4.56 (m, 3 H), 3.91 (s, 3 H), 3.41 (dd, J=13.43, 6.10 Hz, 1 H), 3.24 (dd, J=13.43, 9.16 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 67-68

24
[ 3364-80-5 ]
(2S)-2-amino-3-(4-fluorophenyl)-N-(1-methyl-3-(2-methylpyridin-4-yl)-1H-pyrazol-5-yl)propanamide ditrifluoroacetic acid salt [ No CAS ]
(2S)-3-(4-fluorophenyl)-N-(1-methyl-3-(2-methylpyridin-4-yl)-1H-pyrazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		(2S)-3-(4-Fluorophenyl)-N-(l-methyl-3-(2-methylpyridin-4-yl)-lH- pyrazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide (16.1). To a 100 ml flask was added (2S)-2-amino-3-(4-fluorophenyl)-N-(l-methyl-3-(2 -methylpyridin-4-yl)- lH-pyrazol-5- yl)propanamide TFA (85 mg, 0.182 mmoles), 5 ml of DCE, DIEA (48 mul, 0.27 mmole, Make sure pH = 7), 50 ul of AcOH and <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (16 mg, 0.15 mmole). The reaction was stirred at 65°C for 5 minutes at which time sodium triacetoxyborohydride (116 mg, 0.55 mmoles) was added and stirred at 65 0C for an additional 30 minutes. The solvent was then removed and the crude purified by reverse phase preparative HPLC to give (2S)-2-amino-3- (4-fluorophenyl)-N-( 1 -methyl-3 -(2-methylpyridin-4-yl)- 1 H-pyrazol-5 -yl)propanamide HCl (27.8 mg, 34percent yield) after salt exchange using 1 M HCl in ether (546 ul, 0.55 mmole). LCMS ESI (pos.) m/e: 451.1 (M+l): IH NMR (500 MHz, MeOH-J) delta ppm 9.04 (d, J=I.22 Hz, 1 H) 8.50 (d, J=6.11 Hz, 1 H) 8.16 (s, 1 H) 8.11 (d, J=6.11 Hz, 1 H) 7.78 (s, 1 H) 7.25 (dd, J=8.19, 5.26 Hz, 2 H) 6.95 - 7.10 (m, 3 H) 4.44 (s, 2 H) 4.41 (dd, J=8.93, 5.99 Hz, 1 H) 3.56 (s, 3 H) 3.40 (dd, J=13.33, 5.50 Hz, 1 H) 3.15 (dd, J=13.57, 9.41 Hz, 1 H) 2.70 (s, 3 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 70-71

25
[ 3364-80-5 ]
[ 1240522-05-7 ]
[ 1240522-08-0 ]

Yield	Reaction Conditions	Operation in experiment
53%		S)-N-(l-Methyl-3-(pyridin-4-yl)-lH-pyrazol-5-yl)-3-phenyl-2-(thiazol-4- ylmethylamino)propanamide (17.2). To a rt solution of 17.1 (150 mg, 0.47 mmol) and <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (available from Combi-Blocks Inc.) (48 mg, 0.42 mmol) in1 ,2-dichloroethane (5.0 mL) was added 5percent HO Ac/1, 2- dichloroethane (0.1 mL) followed by sodium triacetoxyborohydride (248 mg, 867 mumol). After stirring at 60 0C for 35 mins, the reaction mixture was quenched with saturated NaHCO3 (4 mL), diluted with water (10 mL) and extracted by 1PrOHZCHCl3 (1 :1, 3 x 10 mL). The organic solvent was removed under reduced pressure. After purification of the residue by preparative HPLC (10-90percent CH3CN/water, 30 min), the combined product fractions was treated with saturated aqueous NaHCO3, extracted with 30percent 1PrOH /CHCl3 and concentrated to provide the title product 17.2 (104 mg, 53percent) as white solid. MS ESI (pos.) m/e: 419.1 (M+H); 1H NMR (400 MHz, CD3OD) delta ppm 3.08 (s, 2 H) 3.61 (s, 3 H) 3.68 (s, 1 H), 3.97 (s, 2 H) 6.73 (s, 1 H), 7.28 (m, 6 H), 7.78 (m, 2 H), 8.53 (m, 2 H), 8.97 (s, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 73-74

26
[ 3364-80-5 ]
[ 1240523-33-4 ]
[ 1240523-46-9 ]

Yield	Reaction Conditions	Operation in experiment
		(2S)-N-(3-(2-Aminopyridin-4-yl)phenyl)-3-phenyl-2-(thiazol-4- ylmethylamino)propanamide (36). To a solution of tert-butyl (S)-l-(3-(2-aminopyridin-4- yl)phenylamino)-l-oxo-3-phenylpropan-2-ylcarbamate (36.C) (200 mg, 0.46 mmol) in THF (2 mL) was added 4M HCl in dioxane (2 mL, 8 mmol). The mixture was stirred at room temperature for 2 hours and then was concentrated. The residue was neutralized with saturated aqueous NaHCO3 and extracted with 4:1 DCM/isopropanol. The organic layers were combined, washed with brine, dried on MgSO4 and concentrated. The residue was dissolved in DCM and then <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (56 mg, 0.50 mmol) was added. The mixture was stirred for Ih at room temperature at which time acetic acid (28 muL, 0.46 mmol) and sodium triacetoxyborohydride (293 mg, 1.38 mmol) were added. The mixture was stirred at room temperature for additional 2 hours, concentrated and the residue purified by reverse phase preparative HPLC to afford (2S)-N-(3-(2-aminopyridin-4-yl)phenyl)-3-phenyl-2- (thiazol-4-ylmethylamino)propanamide 36 (58 mg, 29percent yield) as a white solid. LCMS ESI (pos.) m/e: 430.1 (M+l): IH NMR (400 MHz, MeOH-D4) delta ppm 9.12 (d, J=I.96 Hz, 1 H), 7.91 - 7.97 (m, 2 H), 7.79 (d, J=1.96 Hz, 1 H), 7.42 - 7.57 (m, 3 H), 7.25 - 7.36 (m, 5 H), 7.18 - 7.21 (m, 1 H), 7.13 - 7.17 (m, 1 H), 4.42 - 4.54 (m, 2 H), 4.25 (dd, J=9.39, 5.87 Hz, 1 H), 3.42 (dd, J=13.30, 5.87 Hz, 1 H), 3.25 (dd, J=13.30, 9.00 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 121

27
[ 3364-80-5 ]
[ 1240523-57-2 ]
(S)-3-(3-phenyl-2-(thiazol-5-ylmethylamino)propanamido)-5-(pyridin-4-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		(S)-3-(3-Phenyl-2-(thiazol-5-ylmethylamino)pr opanamido)-5-(pyridin-4- yl)benzoic acid (45.2). To a solution of (S)-3-(2-amino-3-phenylpropanamido)-5-(pyridin-4- yl)benzoic acid (45.1) (181 mg, 0.50 mmol) in DCM (5 mL) was added thiazole-4- carbaldehyde (56 mg, 0.50 mmol). The mixture was stirred for Ih, sodium triacetoxyborohydride (212 mg, 1.00 mmol) was then added and the mixture stirred for an additional 1 hour at room temperature. The reaction mixture was then concentrated and the crude product purified by reverse phase chromatography (0-100percent CHsCN/water + 0.5percent TFA) to afford (S)-3-(3-phenyl-2-(thiazol-5-ylmethylamino)propanamido)-5-(pyridin-4-yl)benzoic acid (45.2) as a white solid (82 mg, 36percent yield). LCMS ESI (pos.) m/e: 459.0 (M+l). IH NMR (500 MHz, MeOH-D4) delta ppm 9.13 (d, J=I.96 Hz, 1 H), 8.93 (d, J=6.85 Hz, 2 H), 8.35 (d, J=I.22 Hz, 1 H), 8.32 - 8.34 (m, 2 H), 8.31 (t, J=I.83 Hz, 1 H), 8.18 - 8.23 (m, 1 H), 7.82 (d, J=I.96 Hz, 1 H), 7.23 - 7.37 (m, 5 H), 4.48 - 4.58 (m, 2 H), 4.35 (dd, J=9.29, 5.87 Hz, 1 H), 3.41 - 3.51 (m, 1 H), 3.24 - 3.30 (m, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 132
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 5942 - 5947,6

28
[ 3364-80-5 ]
[ 1240521-28-1 ]
[ 1240521-30-5 ]

Yield	Reaction Conditions	Operation in experiment
9%	With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 70℃; for 12h;	(S)-3-(4-Chlorophenyl)-N-(3-(pyridin-4-yl)isoxazol-5-yl)-2-(thiazol-4- ylmethylamino)propanamide (3.1). To a 20 ml vial were added (S)-2-amino-3-(4- chlorophenyl)-N-(3-(pyridin-4-yl)isoxazol-5-yl)propanamide 3.1.C (50 mg, 0.15 mmole), <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (20 mg, 0.18 mmole), sodium triacetoxyborohydride (62 mg, 0.29 mmole), 5 ml of DCE, and DIEA (97 mul, 0.15 mmole). The reaction was stirred at 700C for 12 hours. The reaction was then partitioned between 10 ml of water and 20 ml of DCM and the solvent was removed by rotary evaporation. The crude was purified using reverse phase preparative HPLC to give 5.55 mg of (S)-3-(4-chlorophenyl)-N-(3-(pyridin-4-yl)isoxazol-5- yl)-2-(thiazol-4-ylmethylamino)propanamide TFA salt 3.1 as a clear film (5.6 mg, 9percent yield). LCMS ESI (pos.) m/e: 440.1 (M+l): IH NMR (500 MHz, MeOH) delta ppm 9.01 (d, J=I.71 Hz, 1 H), 8.76 - 8.78 (m, 2 H), 8.19 (d, J=6.60 Hz, 2 H), 7.69 (dd, J=13.82, 8.68 Hz, 1 H), 7.24 (d, J=I.96 Hz, I H), 7.13 (d, J=8.3 I Hz, 2 H), 6.99 (d, J=8.31 Hz, 2 H), 4.35 - 4.45 (s, 1 H), 4.26 (m, 2 H), 3.34 (dd, J=8.56, 5.87 Hz, 1 H), 3.17 (dd, J=13.69, 5.87 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 37-38

29
[ 3364-80-5 ]
[ 1240524-14-4 ]
[ 1240524-17-7 ]

Yield	Reaction Conditions	Operation in experiment
8%		(S)-5-(l-(3-Phenyl-2-(thiazol-4-ylmethylamino)propanoyl)-6-(pyridin-4- yl)indolin-4-yl)-l,3,4-oxadiazol-2(3H)-oneTFA salt (57). To a 20 ml flask were added (S)-5-(l-(2-amino-3-phenylpropanoyl)-6-(pyridin-4-yl)indolin-4-yl)-l,3,4-oxadiazol-2(3H)- one TFA salt 57.1.C (80 mg, 0.19 mmole), 10 ml of DCE, DIEA (To pH = 7), thiazole-4- carbaldehyde (21 mg, 0.19 mmole). The reaction was stirred for 2 hour at which time sodium triacetoxyborohydride (119 mg, 0.56 mmole) was added and stirred for an additional 16 hours. The reaction was partitioned between DCM and water. The solvent was removed by rotary evaporation and the crude purified by reverse phase HPLC to (S)-5-(l-(3-phenyl-2- (thiazol-4-ylmethylamino)propanoyl)-6-(pyridin-4-yl)indolin-4-yl)- 1 ,3 ,4-oxadiazol-2(3H)- oneTFA salt 57 as a white solid (7.4 mg, 8 percent yield). IH NMR (400 MHz, MeOH) delta ppm 9.10 (d, J=1.96 Hz, 1 H), 8.81 - 8.87 (m, 3 H), 8.17 (d, J=5.09 Hz, 2 H), 8.03 (d, J=1.56 Hz,1 H), 7.82 (d, J=I.96 Hz, 1 H), 7.31 (s, 5 H), 4.73 (dd, J=IO.17, 5.48 Hz, 1 H), 4.49 - 4.58 (m,2 H), 4.07 (td, J=10.17, 6.26 Hz, 1 H), 3.47 (dd, J=12.91, 5.09 Hz, 1 H), 3.35 - 3.43 (m, 1 H), 3.28 (dd, J=13.11, 9.98 Hz, 1 H), 3.07 - 3.16 (m, 1 H), 2.93 - 3.05 (m, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 154-155

30
[ 3364-80-5 ]
[ 1240524-19-9 ]
[ 1240524-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol; dichloromethane; at 55℃; for 1h;	(S)-3-Phenyl-l-(6-(pyridin-4-yl)-4-(5-thioxo-4,5-dihydro-l,3,4-oxadiazol-2-yl)indolin-l-yl)-2-(thiazol-4-ylmethylamino)propan-l-one (58). To a flask with (S)-2-amino-3-phenyl-l-(6-(pyridin-4-yl)-4-(5-thioxo-4,5-dihydro-l,3,4-oxadiazol-2- yl)indolin-l-yl)propan-l-one 58.C (41 mg, 0.092 mmol) was added <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (13 mg, 0.111 mmol). Then 1 mL MeOH and 0.8 mL dichloromethane were added followed by sodium cyanoborohydrre (17.5 mg, 0.28 mmol). The reaction was heated to 55 degree for 1 hour. Two drops of water was added and reaction was concentrated and purified on reverse phase HPLC to afford 30 mg (42percent) TFA salt of 58. IH NMR (400 MHz, MeOH) delta ppm 9.08 (d, J=1.96 Hz, 1 H) 8.81 - 8.91 (m, 3 H) 8.21 (d, J=6.65 Hz, 2 H) 8.11 (d, J=1.56 Hz, 1 H) 7.81 (d, J=1.96 Hz, 1 H) 7.26 - 7.34 (m, 5 H) 4.73 (dd, J=10.17, 5.09 Hz, 1 H) 4.47 - 4.59 (m,2 H) 4.08 (td, J=10.07, 6.46 Hz, 1 H) 3.47 (dd, J=12.91, 5.48 Hz, 1 H) 3.35 - 3.44 (m, 1 H) 3.22 - 3.30 (m, 1 H) 3.12 (td, J=9.88, 5.67 Hz, 1 H) 2.93 - 3.07 (m, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 156-157

31
[ 3364-80-5 ]
[ 1240524-28-0 ]
[ 1240524-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 70℃; for 76h;	(S)-l-(3-Phenyl-2-(thiazol-4-ylmethylamino)propanoyl)-6-(pyridin-4- yl)indoline-4-carboxamide (60). To a 100 ml flask were added (S)-l-(2-amino-3- phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxamide 61.C (49 mg, 0.13 mmole), thiazole-5-carbaldehyde (16 mg, 0.14 mmole), sodium triacetoxyborohydride (49 mg, 0.23 mmole), 20 ml of DCE, and DIEA (30 mul, 0.17 mmole). The reaction was stirred at 7O0C for 4 hours at which time an additional 50 mg of sodium triacetoxyborohydride was added and stirred for an additional 72 hours. The reaction mixture was then partitioned between CH2Cl2 and water and the solvent was removed from the organic layer by rotary evaporation. The crude product was purified by reverse phase preparative HPLC to give (S)- l-(3-phenyl-2-(thiazol-4-ylmethylamino)propanoyl)-6-(pyridin-4-yl)indoline-4-carboxamide TFA salt 60 as light yellow solid (6.6 mg, 12 percent yield). LCMS ESI (pos.) m/e: 484.1 (M+l) IH NMR (500 MHz, MeOH) delta ppm IH NMR (500 MHz, MeOH), delta ppm 9.10 (d, J=1.96 Hz, 1 H), 8.87 - 8.96 (m, 3 H), 8.37 (d, J=6.85 Hz, 2 H), 8.03 (d, J=I.71 Hz, 1 H), 7.83 (d, J=I.96 Hz, 1 H), 7.24 - 7.37 (m, 5 H), 4.74 (dd, J=10.27, 5.14 Hz, 1 H), 4.46 - 4.60 (m, 2 H), 3.96 - 4.07 (m, 1 H), 3.48 (dd, J=12.96, 4.89 Hz, 1 H), 3.35 - 3.41 (m, 1 H), 3.28 (dd, J=12.96, 10.27 Hz, 1 H), 2.97 - 3.07 (m, 2 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 159-160

32
[ 3364-80-5 ]
[ 1240524-39-3 ]
[ 1240524-41-7 ]

Yield	Reaction Conditions	Operation in experiment
60%		(S)-2-(3-(3-(4-Chlorophenyl)-2-(thiazol-4-ylmethylamino)propanamido)-5-(pyridin-4-yl)phenyl)-2-methylpropanoic acid (63.1). To a 100 ml flask were added (S)-2-(3-(2-amino-3-(4-chlorophenyl)propanamido)-5-(pyridin-4-yl)phenyl)-2- methylpropanoic acid TFA salt 63.1.C (200 mg, 0.36 mmole), <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (33 mg, 0.21 mmole) , sodium triacetoxyborohydride (154 mg , 0.73 mmole), 20 ml of DCE, 1 ml MeOH and DIEA (95 mul, 0.54 mmole). The reaction was stirred at 70 0C for 2 hours at which time sodium cyanotrihydroborate (46 mg, 0.73 mmole) was added and stirred at 70 0C for an additional 1 hour. The reaction mixture was then partitioned between CH2Cl2 and water and the solvent was removed from the organic layer by rotary evaporation. The crude product was purified by reverse phase preparative HPLC to give (S)-2-(3-(3-(4- chlorophenyl)-2-(thiazol-4-ylmethylamino)propanamido)-5-(pyridin-4-yl)phenyl)-2- methylpropanoic acid TFA salt 63.1 as an off white solid (72.5 mg, 60percent yield). LCMS ESI (pos.) m/e: 535.2 (M+l): IH NMR (500 MHz, MeOH) delta ppm 9.14 (d, J=1.96 Hz, 1 H), 8.79 - 8.91 (m, 2 H), 8.14 - 8.25 (m, 2 H), 7.99 (t, J=I.71 Hz, 1 H), 7.82 (d, J=I.96 Hz, 1 H), 7.69 (t, J=I.59 Hz, 1 H), 7.52 (t, J=I.71 Hz, 1 H), 7.35 (m, 2 H), 7.27 (m, 2 H), 4.43 - 4.63 (m, 2 H), 4.28 (dd, J=9.29, 5.87 Hz, 1 H), 3.45 (dd, J=13.45, 5.62 Hz, 1 H), 3.24 (dd, J=13.33, 9.41 Hz, 1 H), 1.65 (d, J=6.85 Hz, 6 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 163

33
[ 3364-80-5 ]
[ 1240524-46-2 ]
[ 1240524-47-3 ]

Yield	Reaction Conditions	Operation in experiment
83%		(2S)-N-(2-hydroxy-5-(2-methylpyridin-4-yl)phenyl)-3-phenyl-2-(thiazol-4- ylmethylamino)propanamide (64.D). Amine 64.C (310 mg, 0.9 mmol), thiazole-4- carboxaldehyde (101 mg, 0.9 mmol), AcOH (51 muL, 0.9 mmol), and NaBH(OAc)3 were stirred in DCM (10 ml) overnight. The reaction mixture was diluted with DCM and neutralized with NaHCO3 (sat). The organic layer was dried with sodium sulfate, filtered, and concentrated to yield 64.D (330 mg, 83percent). LC-MS (+esi, M+H+=445.1). IH NMR (400 MHz, DMSO-J6) delta ppm 10.43 (br. s., 1 H) 9.88 (s, 1 H) 8.99 (d, J=I.96 Hz, 1 H) 8.53 (d, J=2.45 Hz, 1 H) 8.44 (d, J=5.38 Hz, 1 H) 7.41 (s, 1 H) 7.33 - 7.40 (m, 3 H) 7.18 - 7.31 (m, 5 H) 6.97 (d, J=8.31 Hz, 1 H) 3.74 - 3.89 (m, 2 H) 3.53 - 3.62 (m, 1 H) 3.10 (dd, J=13.69, 4.89 Hz, 1 H) 2.87 (dd, J=13.69, 8.31 Hz, 1 H) 2.68 (d, J=6.36 Hz, 1 H) 2.51 (s, 3 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 164

34
[ 3364-80-5 ]
[ 1240521-37-2 ]
[ 1240521-38-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 70℃; for 12h;	3.3.C 3.3[0210] (S)-3-Phenyl-N-(3-(pyridin-4-yl)isoxazol-5-yl)-2-(thiazol-4- ylmethylamino)propanamide (3.3). To a 20 ml vial were added (S)-2-amino-3-phenyl-N- (3-(pyridin-4-yl)isoxazol-5-yl)propanamide 3.3.C (40 mg, 0.13 mmole), thiazole-4- carbaldehyde (18 mg, O.lbetammole), sodium triacetoxyborohydride (55 mg, 0.26mmole) and 10 ml of DCE. The reaction was stirred at 700C for 12 hours. The crude material was partitioned between DCM and water and then purified by reverse phase preparative HLPC to give (S)-3-phenyl-N-(3-(pyridin-4-yl)isoxazol-5-yl)-2-(thiazol-4- ylmethylamino)propanamide TFA salt 3.3 as a white solid (14.2 mg, 27 percent yield). LCMS ESI (pos.) m/e: 406.1 (M+l): IH NMR (500 MHz, MeOH-J) delta ppm 9.09 (d, J=I.96 Hz, 1 H), 8.87 (br. s., 2 H), 8.27 (d, J=5.38 Hz, 2 H), 7.77 (d, J=I.96 Hz, 1 H), 7.27 - 7.35 (m, 3 H), 7.20 - 7.25 (m, 2 H) 7.07 (s, 1 H), 4.42 - 4.55 (m, 2 H), 4.35 (dd, J=8.80, 5.87 Hz, 1 H), 3.44 (dd, J=13.57, 5.99 Hz, 1 H), 3.26 (dd, J=13.69, 8.80 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 41

35
[ 3364-80-5 ]
[ 1240521-41-8 ]
[ 1240521-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 60℃; for 0.5h;	(S)-3-Phenyl-N-(2-(pyridin-4-yl)thiazol-4-yl)-2-(thiazol-4- ylmethylamino)propanamide (4). To a rt solution of 4.C (100 mg, 0.31 mmol) and <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (available from Combi-Blocks Inc.) (34.9 mg, 0.31 mmol) in 1 ,2-dichloroethane was added sodium triacetoxyborohydride (available from Fluka Chemie GmbH) (196 mg, 0.93 mmol) followed by 5percent HOAc/1,2- dichloroethane (50 muL). After stirring at 60 0C for 30 min, the reaction mixture was poured into saturated aqueous NaHCO3 (1.0 mL), diluted with water (5 mL), and extracted with 30percent 1PrOHZCHCl3 (3 x 10 mL). The organic solvent was removed under reduced pressure. After purification of the residue by preparative HPLC (10-90percent CH3CN/water, 30 min), the title product 2 (30 mg, 23percent) was obtained as colorless TFA salt. MS ESI (positve.) m/e: 422.0 (M+H); 1U NMR (400 MHz, CD3OD) delta ppm 2.86 - 3.05 (m, 1 H), 3.12 (dd, J=13.30, 6.26 Hz, 1 H), 3.65 (dd, J=7.83, 6.26 Hz, 1 H), 3.79 - 4.03 (m, 2 H), 7.13 - 7.36 (m, 6 H), 7.84 (s, 1 H), 7.89 - 7.99 (m, 2 H), 8.64 (dd, J=4.50, 1.76 Hz, 2 H), 8.90 (d, J=2.35 Hz, 1 H).

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 42-43

36
[ 3364-80-5 ]
[ 1240521-49-6 ]
[ 1240521-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 4h;	(S)-3-Phenyl-N-(2-(pyridin-4-yl)thiazol-5-yl)-2-(thiazol-4-ylmethylamino)- propanamide (5.3). To a mixture of (S)-2-amino-3-phenyl-N-(2-(pyridin-4-yl)thiazol-5- yl)propanamide (0.075 g, 0.23 mmol), <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (0.026 g, 0.23 mmol) and N,N-dimethylformamide (0.500 ml, 0.23 mmol) in 1 ,2-dichloroethane (1.000 ml, 0.23 mmol) was added sodium triacetoxyborohydride (0.17 g, 0.81 mmol). The resulting mixture was allowed to stir at room temperature for 4 hours. Upon completion, the mixture was directly subjected to HPLC purification give 10 mg of (S)-3-phenyl-N-(2-(pyridin-4-yl)thiazol-5-yl)- 2-(thiazol-4-ylmethylamino)-propanamide 5.3. 400 MHz 1H NMR (CD3OD) delta: 9.30 (d, IH), 8.81 (d, 2H), 8.07 (d, 2H), 7.95 (d, IH), 7.76 (s, IH), 7.28 - 7.37 (m, 3H), 7.24 (dd, J = 8.0, 4.0 Hz, 2H), 4.49 (d, J = 16 Hz, IH), 4.44 (d, J = 16 Hz, IH), 4.43 (dd, J = 12, 8.0 Hz, IH), 3.49 (dd, J = 12, 4.0 Hz, IH), 3.23 (dd, J = 12, 8.0 Hz, IH). LCMS (ES+) m/z 422.

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 47

37
[ 3364-80-5 ]
[ 1240521-60-1 ]
[ 1240521-61-2 ]

Yield	Reaction Conditions	Operation in experiment
37%		(2S)-N-(5-(2-methylamino)pyridine-4-yl)-l,3,4-thiadiazol-2-yl)-3-phenyl- 2-(thiazol-4-ylmethylamino)propanamide (8.1). To a flask with 69 mg of 8.1.F (0.19 mmol) was added <strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (23 mg, 0.2 mmol), 2 niL MeOH and 1 mL dichloromethane. Then sodium cyanoborohydride (24 mg, 0.49 mmol) was added. The reaction mixture was heated at 50 0C for 1 hour. 2 drops of water were added and the reaction was concentrated and purified on reverse phase HPLC column to afford 32 mg of 8.1 (37percent yield). IH NMR (400 MHz, MeOH) delta ppm 8.90 (d, J=I.96 Hz, 1 H) 8.06 (d, J=4.70 Hz, 1 H) 7.31 (d, J=I.96 Hz, 1 H) 7.16 - 7.28 (m, 5 H) 7.03 (dd, J=5.48, 1.56 Hz, 1 H) 6.96 - 7.00 (m, 1 H) 3.92 (d, J=5.09 Hz, 2 H) 3.78 (t, J=7.04 Hz, 1 H) 3.10 (dd, J=12.00, 8.00 Hz, 1 H) 3.01 (dd, J=12.00, 8.00 Hz, 1 H) 2.92 (s, 3 H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6218 - 6223
[2]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 52

38
[ 3364-80-5 ]
[ 1034-49-7 ]
[ 111600-89-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 36; 4-((Z)-2-Tritylthioethen-1-yl)thiazole; a) 4-Ethynylthiazole; Bromomethyltriphenylphosphonium bromide (9.83 g) was added to 100 ml of a suspension of 7.27 g of potassium-t-butoxide in THF under ice cooling, the suspension was stirred at the same temperature for 10 min, and 2.44 g of 4-formylthiazole was further added thereto. The mixture was stirred at room temperature for 2 hr. Thereafter, 100 ml of ethyl acetate and 100 ml of semi-saturated brine were added thereto, followed by separation. The organic layer was then washed with semi-saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane:hexane=3:2) to give 614 mg of 4-ethynylthiazole. NMR (CDCl3) delta: 3.15 (1H, s), 7.58 (1H, d, J=2.0 Hz), 8.78 (1H, d, J=2.0 Hz)

Reference： [1]Patent: US2007/4700,2007,A1 .Location in patent: Page/Page column 22

39
[ 3364-80-5 ]
[ 7036-04-6 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	With methanol; sodium tetrahydroborate; at 0℃; for 1h;	To a solution of thiazole-4-carboxaldehyde (0.810 ml, 9.67 mmol, Combi-Blocks Inc.) in MeOH (48.3 ml) at 0 °C was added sodium borohydride (0.341 ml, 9.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in portions. The reaction mixture was allowed to stir for 1 hour. Saturated aqueous ammonium chloride solution was carefully added and the reaction mixture was filtered. The filtrate was concentrated in vacuo. The solid was taken up in 10percent MeOH/DCM and filtered through a plug of silica gel to provide thiazol- 4-ylmethanol (0.826 g, 7.18 mmol, 74.3percent yield) as a yellow oil. MS m/z = 116.0 [M+H]+. Calculated for C4H5NOS: 115.009. H NMR (400 MHz, CHLOROFORM -J) delta ppm 2.58 (br. s., 1 H) 4.86 (s, 2 H) 7.27 - 7.30 (m, 1 H) 8.83 (d, J=l .76 Hz, 1 H)
	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 2h;	To a solution of sodium borohydride (502 mg, 13.3 mmol) in methanol (20 mL) was added a solution of l,3-<strong>[3364-80-5]thiazole-4-carbaldehyde</strong> (1.0 g, 8.8 mmol) in methanol (5 mL) at 0°C. The mixture was stirred for 2 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, l,3-thiazole-4-ylmethanol was obtained as a yellow oil (596 mg, 58percent yield) and used in the next step without purification; 1HNMR (400 MHz, CDCl3): delta 2.67 (bs, IH), 4.85 (d, J = 5.9 Hz, 2H), 7.28 (s, IH), 8.81 (s, IH).

Reference： [1]Patent: WO2014/138484,2014,A1 .Location in patent: Page/Page column 167; 168
[2]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 137

40
[ 3364-80-5 ]
[ 1314037-50-7 ]
[ 1314037-53-0 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 6216 - 6225

41
[ 3364-80-5 ]
[ 1314037-51-8 ]
[ 1314037-54-1 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 6216 - 6225

42
[ 3364-80-5 ]
[ 1314037-52-9 ]
[ 1314037-55-2 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 6216 - 6225

43
[ 3364-80-5 ]
[ 7357-70-2 ]
[ 1187543-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In ethanol; at 20℃;	Example 3A2-Amino-6-sulfanyl-4-(1,3-thiazol-4-yl)pyridine-3,5-dicarbonitrile492 mg (4.349 mmol) of <strong>[3364-80-5]1,3-<strong>[3364-80-5]thiazole-4-carbaldehyde</strong></strong>, 871 mg (8.697 mmol) of 2-cyanoethanethioamide and 880 mg (8.697 mmol) of N-methylmorpholine were dissolved in 10 ml of ethanol.The reaction mixture was stirred at room temperature overnight, the solvent was removed under reduced pressure and acetonitrile was added to the residue.The solid was filtered off and washed with acetonitrile, and the filter cake was dried under reduced pressure.This gave 181 mg (14percent of theory, 86percent pure) of the target compound.LC-MS (Method 1): Rt=0.76 min; MS (ESIpos): m/z=260 [M+H]+.

Reference： [1]Patent: US2011/207698,2011,A1 .Location in patent: Page/Page column 23-24

44
[ 3364-80-5 ]
[ 439692-56-5 ]
[ 439691-25-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2011,vol. 59,p. 991 - 1002

45
[ 3364-80-5 ]
[ 68076-36-8 ]
[ 1335288-08-8 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 9792 - 9794

46
[ 3364-80-5 ]
[ 141-97-9 ]
[ 57-13-6 ]
[ 1372469-21-0 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 424 - 433
[2]RSC Advances,2016,vol. 6,p. 67072 - 67085

47
[ 3364-80-5 ]
[ 615-43-0 ]
[ 1848-82-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 9577 - 9583

48
[ 3364-80-5 ]
[ 1356458-21-3 ]
[ 1356458-22-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 847 - 854

49
[ 3364-80-5 ]
[ 1356458-16-6 ]
[ 1356458-17-7 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 847 - 854

50
[ 40499-83-0 ]
[ 3364-80-5 ]
[ 1341637-28-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

51
[ 3364-80-5 ]
[ 104-92-7 ]
C₁₁H₁₁NO₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

52
[ 3364-80-5 ]
[ 1365627-53-7 ]
[ 1365626-44-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

53
[ 3364-80-5 ]
C₂HF₃O₂*C₂₀H₂₄N₄O₂ [ No CAS ]
[ 1365626-48-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

54
[ 3364-80-5 ]
[ 45347-82-8 ]
[ 1339049-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

55
[ 3364-80-5 ]
[ 108612-54-0 ]
[ 1365627-67-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2052 - 2062

56
[ 3364-80-5 ]
[ 589-15-1 ]
[ 1383385-52-1 ]

Yield	Reaction Conditions	Operation in experiment
		[623] Example 158 - 3-ri-Methyl-5-(4-methyl-cvclohexyl)-l,2,3,6-tetrahydro-pyridin-4-yl1-5-r4-; [624] A mixture of 4-bromobenzyl bromide (1.00 g, 4.00 mmol) and triphenylphosphine (1.70 g, 6.00 mmol) in toluene (10 mL) was stirred at 80 °C overnight. The reaction mixture wasconcentrated, followed by sonication in hexane, filtration, and a subsequent hexane wash gave a white solid, which was dried in vacuo. This white solid (906 mg, 1.77 mmol) was dissolved in THF (10 mL), cooled to 0 °C, and lithium hexamethyl disilazide (1 M) in THF (1.95 mL, 1.95 mmol) was added. After 0.5 hr, thiazole-4-carboxaldehyde (200 mg, 1.77 mmol) was added, the ice bath was removed, and the mixture stirred for 0.5 hr. The reaction mixture was quenched by the addition of water, extracted with EtOAc (2x30 mL), the organic layer was washed with brine, dried over MgS04, concentrated and filtered through a silica plug using 30percent -100percent EtOAc/hexane to give 158A as a clear oil. MS calcd: M+H)+ = 267. + = 267.

Reference： [1]Patent: WO2012/83105,2012,A1 .Location in patent: Page/Page column 136

57
[ 3364-80-5 ]
[ 1383385-07-6 ]
[ 1383385-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 2h;	[374] Example 61 - 3-ri-Ethyl-5-(4-methyl-cyclohexyl -l,2,3,6-tetrahydro-pyridin-4-yl1-5-\|4-; [375] Thiazole-4-carbaldehyde (17 mg, 0.11 mmole), sodium triacetoxyborohydride (70 mg, 0.33 mmole), and 018B (48 mg, 0.11 mmole) were mixed in 10 mL of DCE. The reaction was stirred at RT for 2 hr. The reaction mixture was then partitioned between CH2C12 and water. The organic layer was concentrated, and the resulting crude product was purified by column chromatography to give 161A. MS calc + = 536. MS found: (M+H)+ = 536.

Reference： [1]Patent: WO2012/83105,2012,A1 .Location in patent: Page/Page column 89

58
[ 3364-80-5 ]
[ 14369-81-4 ]
[ 1391984-56-7 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 8642 - 8653
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 6402 - 6405

59
[ 3364-80-5 ]
[ 504-02-9 ]
[ 109-77-3 ]
[ 1402044-75-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 851 - 855

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Precautionary Statements-General
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Code	Phrase
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P321
P322
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
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P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H332	Harmful if inhaled
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H361	Suspected of damaging fertility or the unborn child
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H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 3364-80-5 ]

Quality Control of [ 3364-80-5 ]

Related Doc. of [ 3364-80-5 ]

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[ 3364-80-5 ] Synthesis Path-Upstream 1~10

[ 3364-80-5 ] Synthesis Path-Downstream 1~59

Related Functional Groups of [ 3364-80-5 ]

Aldehydes

Related Parent Nucleus of [ 3364-80-5 ]

Thiazoles

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[ 3364-80-5 ]

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[ 3364-80-5 ]