[ CAS No. 6000-43-7 ] {[proInfo.proName]}

Name: 6000-43-7|Glycine hydrochloride|99%
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Quality Control of [ 6000-43-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6000-43-7 ]

SDS Specification

Alternatived Products of [ 6000-43-7 ]

Product Details of [ 6000-43-7 ]

CAS No. :	6000-43-7	MDL No. :	MFCD00012872
Formula :	C₂H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IVLXQGJVBGMLRR-UHFFFAOYSA-N
M.W :	111.53	Pubchem ID :	22316
Synonyms :		Chemical Name :	Glycine hydrochloride

Calculated chemistry of [ 6000-43-7 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	23.17
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-2.41
Log Po/w (WLOGP) :	-0.17
Log Po/w (MLOGP) :	-3.06
Log Po/w (SILICOS-IT) :	-1.04
Consensus Log Po/w :	-1.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.05
Solubility :	1260.0 mg/ml ; 11.3 mol/l
Class :	Highly soluble
Log S (Ali) :	1.62
Solubility :	4650.0 mg/ml ; 41.7 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.83
Solubility :	757.0 mg/ml ; 6.79 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 6000-43-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6000-43-7 ]

* 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 [ 6000-43-7 ]
Downstream synthetic route of [ 6000-43-7 ]

[ 6000-43-7 ] Synthesis Path-Upstream 1~7

1
[ 6000-43-7 ]
[ 98-59-9 ]
[ 1080-44-0 ]

Reference： [1] Acta Universitatis Lundensis, 1892, vol. 28, p. 2.Abt.,Abhandl.III,S.3

2
[ 6000-43-7 ]
[ 122-01-0 ]
[ 13450-77-6 ]

Reference： [1] Die Pharmazie, 2000, vol. 55, # 11, p. 825 - 828

3
[ 67-56-1 ]
[ 6000-43-7 ]
[ 5680-79-5 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2>37, p. 163
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 5, p. 1071 - 1082

4
[ 64-17-5 ]
[ 6000-43-7 ]
[ 623-33-6 ]

Reference： [1] Inorganic Chemistry, 2016, vol. 55, # 11, p. 5592 - 5602

5
[ 111-87-5 ]
[ 6000-43-7 ]
[ 39540-30-2 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 10, p. 708 - 711[2] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 10, p. 1214 - 1217
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5381 - 5390

6
[ 1186048-83-8 ]
[ 6000-43-7 ]
[ 17585-69-2 ]
[ 6003-05-0 ]
[ 17694-98-3 ]
[ 7776-34-3 ]

Reference： [1] Tetrahedron, 2009, vol. 65, # 34, p. 7171 - 7176

7
[ 6000-43-7 ]
[ 2905-61-5 ]
[ 667403-46-5 ]

Reference： [1] Patent: WO2016/155684, 2016, A1, . Location in patent: Page/Page column 2

[ 6000-43-7 ] Synthesis Path-Downstream 1~88

1
[ 64-17-5 ]
[ 80-56-8 ]
[ 6000-43-7 ]
[ 56-40-6 ]

Reference： [1]Patent: US2316215,1941,

2
[ 64-17-5 ]
[ 6000-43-7 ]
[ 459-73-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2>37,p. 163

3
[ 123-51-3 ]
[ 6000-43-7 ]
glycine isopentyl ester; hydrochloride [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2>37,p. 163

4
[ 54090-41-4 ]
[ 6000-43-7 ]
[ 67320-47-2 ]

Reference： [1],1892,vol. 28,p. 2.Abt.,Abhandl.III,S.17

5
[ 18706-82-6 ]
[ 1668-10-6 ]
[ 6000-43-7 ]
[ 18783-59-0 ]

Reference： [1]Chemische Berichte,1968,vol. 101,p. 2189 - 2196

6
[ 6000-43-7 ]
[ 68-12-2 ]
N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium perchlorate [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1973,vol. 38,p. 2633 - 2640
[2]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1504 - 1513

7
[ 6000-43-7 ]
[ 3741-34-2 ]
[ 63972-69-0 ]

Reference： [1]Tetrahedron,1977,vol. 33,p. 635 - 643

8
[ 6000-43-7 ]
[ 49569-57-5 ]
[ 67726-16-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1978,vol. 16,p. 325 - 326

9
[ 66692-88-4 ]
[ 931-53-3 ]
[ 6000-43-7 ]
[ 144686-14-6 ]

Reference： [1]Synthesis,1992,p. 837 - 838
[2]Synthesis,1992,p. 837 - 838

10
[ 13206-47-8 ]
[ 931-53-3 ]
[ 6000-43-7 ]
[ 144686-16-8 ]

Reference： [1]Synthesis,1992,p. 837 - 838

11
[ 13206-47-8 ]
[ 6000-43-7 ]
Acetic acid isocyanomethyl ester [ No CAS ]
[ 144686-18-0 ]

Reference： [1]Synthesis,1992,p. 837 - 838

12
[ 4704-64-7 ]
[ 931-53-3 ]
[ 6000-43-7 ]
cyclohexylaminocarbonyl-4-glycyl-1-thia-4-azaspiro<4.5>decane [ No CAS ]

Reference： [1]Synthesis,1994,p. 619 - 623

13
[ 4704-64-7 ]
[ 119072-55-8 ]
[ 6000-43-7 ]
3-tert-butylaminocarbonyl-4-glycyl-1-thia-4-azaspiro<4.5>decane [ No CAS ]

Reference： [1]Synthesis,1994,p. 619 - 623

14
[ 931-53-3 ]
[ 6000-43-7 ]
2,2-dimethyl-1-oxa-4-azaspiro<4.5>dec-3-ene [ No CAS ]
3-cyclohexylaminocarbonyl-4-glycyl-2,2-dimethyl-1-oxa-4-azaspiro<4.5>decane [ No CAS ]

Reference： [1]Synthesis,1994,p. 619 - 623

15
[ 111-87-5 ]
[ 6000-43-7 ]
[ 39540-30-2 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 708 - 711
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1214 - 1217
[2]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5381 - 5390

16
[ 112-30-1 ]
[ 6000-43-7 ]
[ 39540-28-8 ]

17
[ 112-53-8 ]
[ 6000-43-7 ]
[ 16194-11-9 ]

18
[ 112-72-1 ]
[ 6000-43-7 ]
[ 77338-35-3 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 708 - 711
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1214 - 1217

19
[ 70288-73-2 ]
[ 6000-43-7 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 173 - 189

20
[ 15166-50-4 ]
[ 6000-43-7 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1984,p. 770 - 771

21
[ 367-62-4 ]
[ 6000-43-7 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 420 - 423

22
[ 6000-43-7 ]
[ 79539-35-8 ]
C₁₄H₈N₂O₁₀S₂^(2-)*2K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 7615 - 7620

23
[ 6000-43-7 ]
[ 95911-95-8 ]
[ 95912-12-2 ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 3328

24
[ 67-56-1 ]
[ 6000-43-7 ]
[ 90-02-8 ]
[ 69698-15-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2285 - 2296

25
[ 6000-43-7 ]
[ 501-53-1 ]
[ 1138-80-3 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 2446 - 2452

26
[ 74743-61-6 ]
[ 103-82-2 ]
[ 6000-43-7 ]
[ 88168-76-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1127 - 1132

27
[ 116963-47-4 ]
[ 6000-43-7 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 1603 - 1605

28
[ 6000-43-7 ]
[ 78-84-2 ]
[ 74-89-5 ]
[ 111622-98-1 ]

Reference： [1]Helvetica Chimica Acta,1992,vol. 75,p. 855 - 864

29
[ 1068-90-2 ]
[ 6000-43-7 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 2446 - 2452

30
[ 6000-43-7 ]
[ 3339-63-7 ]
[ 2566-19-0 ]

Reference： [1]Journal of general chemistry of the USSR,1968,vol. 38,p. 2542 - 2545
Zhurnal Obshchei Khimii,1968,vol. 38,p. 2627 - 2630

31
[ 6000-43-7 ]
[ 122-01-0 ]
[ 13450-77-6 ]

Reference： [1]Pharmazie,2000,vol. 55,p. 825 - 828

32
[ 6000-43-7 ]
[ 68-12-2 ]
C₅H₁₃N₂⁽¹⁺⁾*F₆P^(1-)*H⁽¹⁺⁾ [ No CAS ]
N-(3-(dimethylamino)-2-[(dimethylamino)methylene]amino}prop-2-en-1-ylidene)-N-methylmethanaminium hydrogen dihexafluorophosphate [ No CAS ]

Reference： [1]Synthesis,2005,p. 1817 - 1821

33
[ 6000-43-7 ]
[ 68-12-2 ]
N-(3-(dimethylamino)-2-[(dimethylamino)methylene]amino}prop-2-en-1-ylidene)-N-methylmethanaminium hydrogen dihexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		Phosphorus oxychloride (70 ml, 0.75 mol) was added dropwise to dimethylformamide (150 ml) at 1O0C, and the mixture was then stirred for 20 minutes at 2O0C. This solution was cooled o to 50C and powdered glycine hydrochloride (27.9 g, 0.25 mol) was added in portions; the temperature of the reaction mixture was maintained at 2O0C. The mixture was then heated to 80 +/- 20C (internal temperature). The solid rapidly disappeared and there was slight effervescence. After 4 hours, the still hot, dark brown solution was poured directly in a fine stream into water (400 ml), pre-cooled to 50C, the temperature was kept below 2O0C with a s dry ice/isopropanol bath. After stirring the solution for 5 minutes, it was cooled to - 50C and treated from a plastic vessel with 60% aqueous hexafluorophosphoric acid (74 ml, 0.5 mol). A thick precipitate formed immediately and was filtered off, washed with ethanol (500 ml) and air-dried to constant weight over 2 hours. In subsequent runs the product contained up to 0.2 extra equivalents of hexafluorophosphoric acid. o Yield: 73.1 g (60%); off-white solid, mp 165 - 185C decomp.IH NMR (DMSOd6): delta = 10.15 (d, J = 12 Hz, IH); 8.05 (d, J = 12 Hz, IH); 7.67 (s, 2H); 3.27(m, 9H); 3.15 (m, 9H).13C NMR (DMSOd6): delta = 161.11, 158.53, 100.85, 49.17, 43.96, ~ 40 (under DMSO), 36.97.MS: m/z = 197 (M+). 5 Anal. Calcd. for Ci0H22N4-PF6.1.2HPF6: C, 23.2; H, 4.29; N, 10.82. Found: C, 23.46; H, 4.26; N, 10.60.

Reference： [1]Synthesis,2005,p. 1817 - 1821
[2]Patent: WO2007/34183,2007,A2 .Location in patent: Page/Page column 16

34
[ 6000-43-7 ]
[ 530-62-1 ]
C₆H₇N₃O₃ [ No CAS ]

Reference： [1]Synlett,2007,p. 603 - 606

35
[ 6000-43-7 ]
[ 100-46-9 ]
[ 39796-52-6 ]

Reference： [1]Synlett,2007,p. 603 - 606

36
[ 6000-43-7 ]
N-(2-amino-2-oxoethyl)-3-(4-[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 : lambda/-(2-Amino-2-oxoethyl)-3-(4-{r4-r5-fluoro-2-(methyloxy)phenyl1-2-hvdroxy-4- methyl-2-(trifluoromethyl)pentyl1amino>-6-methyl-1 /-/-indazol-1-yl)benzamide; lambda/,lambda/-Diisopropylethylamine (0.109mL, 0.625mmol) was added to a solution of 3-(4-[4-[5- fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl- 1 /-/-indazol-1-yl)benzoic acid (70mg, 0.125mmol) and HATU (47.5mg, 0.125mmol) in DMF (2.5mL) and the solution stirred at room temperature for 5 min. <strong>[6000-43-7]Glycine hydrochloride</strong> (34.6mg, 0.313mmol) was added and the mixture stirred at room temperature overnight and then partitioned between 2M HCI (5OmL) and ethyl acetate (5OmL). The organic layer was separated, washed with aqueous sodium bicarbonate (50ml), dried over anhydrous <n="69"/>sodium sulphate and evaporated to give crude product which was purified by mass directed autopreparation (System B) to give the title compound (62.5mg). LCMS: tRET = 3.59 min; MH+ = 616This racemic material was resolved by chiral HPLC on a 2inch x 20cm Chiralpak AD column eluted with heptane : EtOH 2 : 8 with a flow rate of 75 mL/min to provide Example 1-A (enantiomer A, 15.2mg) and Example 1-B (enantiomer B, 17.5mg)Example 1-A (enantiomer A): Analytical chiral HPLC (25 x 0.46 cm Chiralpak AD column, heptane : EtOH 2 : 8 eluting at 1 mL/min): tREtau = 6.7 min LCMS: tRET = 3.60 min; MH+ = 616Example 1-B (enantiomer B): Analytical chiral HPLC (25 x 0.46 cm Chiralpak AD column, heptane : EtOH 1 : 9 eluting at 1 mL/min): tREtau = 1 1.3 min LCMS: tRET = 3.60 min; MH+ = 616

Reference： [1]Patent: WO2007/122165,2007,A1 .Location in patent: Page/Page column 66-67

37
[ 898552-43-7 ]
[ 6000-43-7 ]
[ 898552-49-3 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; acetonitrile; for 16h;	Chloroform was then added and the mixture was washed twice with 1M HCl, dried over Na2SO4 and the solvents were evaporated under reduced pressure to give an orange solid. Purification was carried out by HPLC using a water:acetonitrile gradient as eluent, to give Compound 18 (202 mg, 85% yield) as a yellow solid. 1H NMR (CDCl3): delta=7.77 (d, 2H), 7.42 (d, 2H), 7.29 (s, 1H), 6.92 (s, 1H), 3.90 (s, 2H), 3.89 (s, 2H), 2.32 (s, 2H), 1.14 (s, 6H); MS (ES+): m/z (%)=538 and 540 (100), 496, 498 (MNa+, 10), 474, 476 (MH+, 58), 399 and 401 (MH+-Gly-OH, 17).

Reference： [1]Patent: US2008/39456,2008,A1 .Location in patent: Page/Page column 48

38
[ 812639-32-0 ]
[ 6000-43-7 ]
[ 812639-33-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine; In methanol; 1,2-Dichloropropane; at 20℃;	<strong>[6000-43-7]Glycine hydrochloride</strong> (2.00 mmol, 251 mg) was added to a solution of methyl-phenyl-carbamic acid 5-isothiocyanato-pyridin-2-yl ester (0.57 g, 2.00 mmol) in 1,2- dichloropropane (5 ml). A few millilitres of methanol were added to get a clear solution.Triethylamine (0.28 ml, 2.00 mmol) was added and the solution was stirred overnight atroom temperature. Dichloromethane was added and the reaction mixture was extracted twicewith water, dried over sodium sulphate, filtered and evaporated in vacuo. The residue waspurified by flash column chromatography (Si02) ethyl acetate/heptane 70/30), yielding thetitle compound (0.27 g, 40% yield) as a solid.1H NMR (300 MHz, CDCI3): 8= 3.46 (br.s, 3H), 4.14 (s, 2H), 7.17 (m, 1H), 7.27 (m, 1H), 7.39(m, 4H), 7.75 (m, 2H), 8.39 (s, 1H); HPLC-MS (Method A): m/z= 375 (M+H)+; Rt = 2.64 min.

Reference： [1]Patent: WO2004/111031,2004,A1 .Location in patent: Page 50-51

39
CH₃O₄PPol₂ [ No CAS ]
[ 6000-43-7 ]
[ 1071-83-6 ]

Yield	Reaction Conditions	Operation in experiment
42%Chromat.	at 180℃; for 16h;	In a series of runs, glyphosate salt was prepared by reaction of dehydrated HMPA and a ten fold excess of each of several glycine acid salts. Three runs were conducted with glycine hydrochloride, one with trifluoroacetic acid salt, and another with the sulfuric acid salt. The conditions of the reactions, HMPA conversions, glycine conversions, and selectivities are shown in Table 10.
49 - 55%Chromat.	at 166 - 171℃; for 16 - 17h;	In a series of runs, glyphosate salt was prepared by reaction of dehydrated HMPA and a ten fold excess of each of several glycine acid salts. Three runs were conducted with glycine hydrochloride, one with trifluoroacetic acid salt, and another with the sulfuric acid salt. The conditions of the reactions, HMPA conversions, glycine conversions, and selectivities are shown in Table 10.

Reference： [1]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 31
[2]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 31

40
[ 2617-47-2 ]
[ 6000-43-7 ]
[ 1071-83-6 ]

Yield	Reaction Conditions	Operation in experiment
42%Spectr.	at 162℃; for 17h;	Additional reactions of glycine hydrochloride and HMPA were conducted under various conditions and, in certain instances, in the presence of various additives. The additives used, reaction conditions and results are shown in Table 11.
23.2%Spectr.	at 152℃; for 16h;Heating / reflux;	Additional reactions of glycine hydrochloride and HMPA were conducted under various conditions and, in certain instances, in the presence of various additives. The additives used, reaction conditions and results are shown in Table 11.
34.7%Spectr.	at 154℃; for 17h;	Additional reactions of glycine hydrochloride and HMPA were conducted under various conditions and, in certain instances, in the presence of various additives. The additives used, reaction conditions and results are shown in Table 11.

43.5%Spectr.

at 162℃; for 17h;Molecular sieve;

Additional reactions of glycine hydrochloride and HMPA were conducted under various conditions and, in certain instances, in the presence of various additives. The additives used, reaction conditions and results are shown in Table 11.

Reference： [1]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 32
[2]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 32
[3]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 32
[4]Patent: US2005/54871,2005,A1 .Location in patent: Page/Page column 32

41
[ 6000-43-7 ]
2-{3-[2-(2,4-dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-benzylamino}-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		To a solution of (2, 4-DICHLORO-PHENYL)- [6- (3-HYDROXYMETHYL-PHENYL)-3-METHYL- BENZOFURAN-2-YL]-METHANONE (100 mg, 0.24 MMOL) in N, N-dimethylformamide (3 mL) at 0C was added triethylamine (49.11 mg, 0.49 MMOL), lithium iodide (39.04 mg, 0.29 MMOL) and METHANESULFONYL CHLORIDE (33.42 mg, 0.29 MMOL). The reaction was aged for 2h at 0C then glycine hydrochloride (40.32 mg, 0. 36MMOL) was added to the solution. The reaction mixture was heated overnight at 50C after which time the reaction was cooled to room temperature and the volatiles were removed under reduced pressure. The crude residue was purified by pre-HPLC to afford 2- {3- [2- (2, 4-DICHLORO-BENZOYL)-3- METHYL-BENZOFURAN-6-YL]-BENZYLAMINO}-ACETAMIDE as a TFA salt. The material was converted to its free base using aqueous sodium bicarbonate and ethyl acetate to give the title material as a yellowish oil (22 mg, 19%). MS ES (MH+ 467.0/469. 0). H-NMR (Acetone d6) 6 7.92 (dd, J = 8 Hz, J = 2 Hz, 1H), 7.83-7. 82 (m, 1H), 7.81-7. 80 (m, 1 H), 7.74 (dd, J = 8 Hz, J = 2 Hz, 1H), 7.70-7. 67 (m, 1H), 7.65 (dt, J = 7 HZ, J = 2 HZ, 1 H), 7.62 (d, J = 2Hz, 1H), 7.60 (d, J = 2Hz, 1H), 7.47-7. 40 (m, 2H), 7.14 (br, 1H), 6.36 (br, 1 H), 3.89 (s, 2H), 3.22 (s, 2H), 2.83 (br, 1 H), 2.62 (s, 3H).

Reference： [1]Patent: WO2005/14566,2005,A1 .Location in patent: Page/Page column 86-87

42
[ 6000-43-7 ]
[ 646517-54-6 ]
[ 646517-57-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris(1,3-dihydro-2-oxobenzoxazolin-3-yl) phosphine oxide; triethylamine; In acetonitrile; at 20℃; for 0.333333h;	To a solution of 54 (42.4 mg, 0.15 mmol) in CH3CN (0. 86 mL) was added tris (2- oxo-3-oxazolinyl) phosphine oxide3 (91 mg, 0.20 mmol), methylglycinate hydrochloride (19.7 mg, 0.16 mmol) and NEt3 (43 I1L, 0.31 mmol) and the solution was allowed to stir at room temperature for 20 minutes. The mixture was poured into a solution of NUH4Cl(sat)/1 N HC1 (10 mL) and extracted with ET20 (3 X 10 ML). The combined organics were dried (MGS04), filtered, evaporated and chromatographed (40-50% EtOAc/Hexanes) to give pure 57 (43 mg, 80%). 1H NMR (300 MHz, CDC13) 8 0.85 (t, J= 6.8 Hz, 3 H), 1.23-1. 26 (m, 7 H), 1.49-1. 55 (m, 1 H), 1.65 (s, 3 H), 1.84-1. 90 (m, 2 H), 3.79 (s, 3 H), 4.11 (d, J= 5 Hz, 1 H), 4.12 (d, J= 5 Hz, 1 H), 4.47 (s, 2 H), 5.36 (s, 1 H), 6.76 (bs, 1 H)

Reference： [1]Patent: WO2004/5277,2004,A1 .Location in patent: Page 38

43
[ 6000-43-7 ]
[ 71-36-3 ]
[ 13048-99-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 70℃;	Step 3: 2-Butoxy-2-oxoethanaminium chloride; <strong>[6000-43-7]Glycine hydrochloride</strong> (400g, 3.58 mol) was suspended in 8 L of n-butanol and thionyl chloride (1.37L, 18.84 mol) was added slowly dropwise (exotherm). After addition was complete, the reaction was heated to 70 C overnight. The reaction could be followed by spotting directly on TLC, pumping off the volatiles, eluting with 10% MeOH/CHC13 saturated with NH3, and staining in ninhydrin. The next day the reaction was stripped to dryness under vacuum and the residue was triturated with heptane/EtOAc to give the product as a white solid after drying on a filter under Nitrogen. 1H NMR (400 MHz, CDC13) 8 8.5 (bs, 3H), 4.18 (t, J = 6.7 Hz, 2H), 4.0 (bs, 2H), 1.62 (m, 2H), 1. 38 (m, 2H), 0. 92 (t, J = 7.4 Hz, 3H) ppm. ES MS M+1 = 132.
	With thionyl chloride; at 70℃;	To a suspension of glycine hydrochloride (400 g, 3.58 mol) in n-butanol (8 L), thionyl chloride (1.37 L, 18.84 mol) was added slowly dropwise. After addition was complete, the reaction was EPO <DP n="53"/>heated at 70 0C overnight. The product mixture was concentrated under vacuum and the residue was triturated with a mixture of heptane/ethyl acetate. The white solid precipitated was filtered and dried under a stream of dry nitrogen to provide the title compound. lHNMR (400 MHz, CDCI3) delta 8.5 (br s, 3H), 4.18 (t, J= 6.7 Hz, 2H), 4.0 (br s, 2H), 1.62 (m, 2H), 1.38 (m, 2H), 0.92 (t, J= 7.4 Hz, 3H). ES MS M+l = 132.
	With thionyl chloride; at 70℃;	To a suspension of glycine hydrochloride (400 g, 3.58 mol) in n-butanol (8 L), thionyl chloride (1.37 L, 18.84 mol) was added slowly dropwise. After addition was complete, the reaction was heated at 70 C overnight. The product mixture was concentrated under vacuum <n="21"/>and the residue was triturated with a mixture of heptane/ethyl acetate. The white solid precipitated was filtered and dried under a stream of dry nitrogen to provide the title compound. lH NMR (400 MHz, CDCI3) delta 8.5 (br s, 3H), 4.18 (t, J= 6.7 Hz, 2H), 4.0 (br s, 2H), 1.62 (m,2H), 1.38 (m, 2H), 0.92 (t, J- 7.4 Hz, 3H). ES MS M+l = 132.

With thionyl chloride; at 70℃;

Step 3: 2-Butoxy-2-oxoethanaminium chloride To a suspension of glycine hydrochloride (400 g, 3.58 mol) in n-butanol (8 L), thionyl chloride (1.37 L, 18.84 mol) was added slowly dropwise. After addition was complete, the reaction was heated at 70 C. overnight. The product mixture was concentrated under vacuum and the residue was triturated with a mixture of heptane/ethyl acetate. The white solid precipitated was filtered and dried under a stream of dry nitrogen to provide the title compound. 1H NMR (400 MHz, CDCl3) delta 8.5 (br s, 3H), 4.18 (t, J=6.7 Hz, 2H), 4.0 (br s, 2H), 1.62 (m, 2H), 1.38 (m, 2H), 0.92 (t, J=7.4 Hz, 3H). ES MS M+1=132.

Reference： [1]Patent: WO2005/87767,2005,A1 .Location in patent: Page/Page column 43-44
[2]Patent: WO2006/121831,2006,A2 .Location in patent: Page/Page column 51-52
[3]Patent: WO2008/48538,2008,A1 .Location in patent: Page/Page column 19-20
[4]Patent: US2008/280945,2008,A1 .Location in patent: Page/Page column 8

44
[ 6000-43-7 ]
[ 71-36-3 ]
[ 590-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 70℃;	EXAMPLE 8; N- [6- (4-fluorobenzyl)-3, 4-dihydroxy-5-oxo-5,6, 7,8-tetrahydro-2, 6-naphthyridin-1-yl]-N- methylmethanesulfonamide; Step 1 : 1- (glycyloxy) butane chloride; To a suspension of glycine hydrochloride (lOg, 89.6 mmol) in 250 mL butanol under nitrogen was added thionyl chloride (45.7 mL, 627 mmol) dropwise. After the addition was complete, the solution was heated at 70 C overnight. The volatile components were removed on the roto-evaporator and the residue was suspended and evaporated from toluene three times. The resulting crude gum was dissolved in an equal weight of toluene for easy transfer and was used as is in the next reaction. 1H NMR (400 MHz, CDCl3). 8 8. 5 (bs, 3H), 4.18 (t, J=6. 7 Hz, 2H), 4.0 (bs, 2H), 1.62 (m, 2H), 1.38 (m, 2H), 0.92 (t, J=7. 4 Hz, 3H) ppm. ES MS M+1 = 132.

Reference： [1]Patent: WO2005/87767,2005,A1 .Location in patent: Page/Page column 30

45
C₃H₇O₄PolS [ No CAS ]
[ 6000-43-7 ]
mPEG-glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In water; at 37℃; for 72h;pH 10.5;	2 g of glycine hydrochloride was dissolved in 20 ml of deionized water. 1 g of NaOH was added to the glycine solution to adjust the pH to 10.5. Then 2 g of mPEG mesylate ester of molecular weight 5000 (obtained from above step) was added to the solution. The solution was incubated at 37 C. for 72 hours, and then neutralized by hydrochloride solution to pH about 7. The polymer was extracted with dichloromethane. The organic phase was dried with anhydrous sodium sulfate and the solvent was removed under vacuum. Yield: 1.7 g (85%), Mp: 55-57 C. NMR (DMSO): 3.5 (br m, H in PEG), 3.24 (s, 3H), 2.95 (t, 2H), 3.11 (s, 2H).

Reference： [1]Patent: US2005/180946,2005,A1 .Location in patent: Page/Page column 4; 6; sheet 3

Yield	Reaction Conditions	Operation in experiment
91.4%		The first and second crops are combined to obtain the desired glycine hydrochloride in a purity of 99% and a yield of 91.4%.
		(a) 100g (1.33 moles) of glycine are added to 150 ml. (1.27 moles) of concentrated hydrochloric acid and the reaction mixture is heated to between 50 and 53 C. The resultant solution is then cooled to between -10 and -8 C. and maintained at that temperature for between 15 and 20 minutes. The resultant solid is then filtered, the filtrate is cooled to -15 C. and maintained at this temperature for about 10 minutes, and then filtered through the same filter. The residue is then dried in a vacuum oven for 18 hours at 90 C. to yield 94g of a first crop of glycine hydrochloride.
		(b) The filtrate from a) above is cooled to 0 C. and to the cooled filtrate is added 60g (1.64 moles) of anhydrous hydrogen chloride, at which time precipitation commences and the temperature of the mixture begins to rise. The reaction mixture is allowed to warm to 23 C. and maintained at this temperature for about 15 minutes. The mixture is then cooled to -15 C. and maintained at this temperature for between 10 and 15 minutes. The resultant solid is then filtered and the residue is dried in a vacuum oven for 18 hours at 90 C. to yield 42g of a second crop of glycine hydrochloride.

47
[ 2439-99-8 ]
[ 6000-43-7 ]
[ 1071-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide;	EXAMPLE 1 Preparation of N-Phosphonomethylglycine To a 50 milliliter (ml) three-necked, round-bottom flask equipped with a magnetic stirrer, a heating mantle, a condenser, and a thermometer was added 2.6 grams (g) (10.0 mole) of N,N-bis(phosphonomethyl)glycine, 9 g (10 mmole) of glycine hydrochloride, and 5 ml of 47% aqueous hydrobromic acid. The solution was then heated to reflux temperature which was approximately 123 C., and was refluxed for a period of 15.5 hours. Thereafter, the solution was cooled, and a sample taken for quantitative analysis by high performance liquid chromatograhy (hplc). The yield of N-phosphonomethylglycine was 2.0 mmole (10% of theory).

Reference： [1]Patent: US4440695,1984,A

48
2-[(2-amino-5-chloro-α-phenylbenzylidene)amino]propanol [ No CAS ]
[ 6000-43-7 ]
2-[(2-Aminoacetamido-5-chloro-α-phenylbenzylidene)amino] propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; N-methyl-acetamide; water;	EXAMPLE 4 2-[(2-Aminoacetamido-5-chloro-alpha-phenylbenzylidene)amino] propanol To a solution of 4.5g of N,N'-dicyclohexylcarbodimide in 100ml of dimethylformamide is added a solution of 2.2g of glycine hydrochloride in 2.2ml of water in a period of about 30 seconds under stirring and ice-cooling. To the reaction mixture is immediately added dropwise a solution of 3.3g of 2-[(2-amino-5-chloro-alpha-phenylbenzylidene)amino]propanol in 10ml of tetrahydrofuran and the mixture is stirred for further 3 hours at room temperature. After the reaction is completed, the reaction mixture is treated by the same manner as described in the Example 1 to give 1.3g of the desired product melting at 168-172 C.

Reference： [1]Patent: US4022832,1977,A

49
[ 865185-41-7 ]
[ 6000-43-7 ]
7-{N-(carboxymethyl)aminomethyl}-5-(3-chlorophenyl)-8-methoxy-2-(methylamino)quinazoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%		Example 93 7-{N-(carboxymethyl)aminomethyl}-5-(3-chlorophenyl)-8-methoxy-2-(methylamino)quinazoline mono hydrochloride (Compound 93) Compound 82 (350 mg, 1.01 mmol) was dissolved in 1,2-dichloroethane (10 mL), and glycine hydrochloride (161 mg, 1.28 mmol) and sodium triacetoxyborohydride (714.8 mg, 3.37 mol) was added thereto, and then the mixture was stirred at room temperature for 8 hours. To the reaction mixture was added water, and the pH of the mixture was adjusted to 2 with 2 mol/L hydrochloric acid. Then, to the mixture was added ethyl acetate and the mixture was separate into an organic layer and an aqueous layer. The pH of the aqueous layer adjusted to 10 with 1 mol/L aqueous sodium hydroxide, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (3.5 mL), and 1 mol/L aqueous sodium hydroxide (1.9 mL) was added thereto, and then the mixture was stirred overnight. After the pH of the reaction mixture was adjusted to 5 with 1 mol/L hydrochloric acid, the precipitated crystal was collected by filtration, and washed with water. The resulting solid was suspended in' ethanol, and 4 mol/L hydrogen chloride - ethyl acetate was added thereto, and the mixture was stirred at room temperature for 1 hour. Then, the solvent was evaporated under reduced pressure. The resulting crystal was triturated with 2-propanol to give Compound 93 (65.9 mg, 15 %) as a yellow solid. 1H NMR (DMSO-d6, delta): 2.51-2.73 (m, 2H), 2.91 (s, 3H), 3.75 (s, 2H), 4.00 (s, 3H), 7.31-7.61 (m, 5H), 8.35 (brs, 1H). APCIMS m/z: [M+H]+ 387.

Reference： [1]Patent: EP1726584,2006,A1 .Location in patent: Page/Page column 56

50
[ 6000-43-7 ]
barium carbonate [ No CAS ]
[ 130769-54-9 ]

Reference： [1]Biochemical Journal,1920,vol. 14,p. 577
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ba: MVol., 7.7, page 207 - 209

51
[ 14283-99-9 ]
[ 6000-43-7 ]
[ 75214-75-4 ]
ammonium chloride [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1989,vol. 165,p. 197 - 200

52
dihydroxopyridoxoliron(III) [ No CAS ]
[ 6000-43-7 ]
Fe₂(Pyr)2(NH₂CH₂COO)2Cl₂ [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1988,vol. 27,p. 318 - 322

53
[ 21673-65-4 ]
[ 6000-43-7 ]
bis(N-salicylideneglycinato)Cu(II) [ No CAS ]
ammonium chloride [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1989,vol. 165,p. 197 - 200

54
[ 6000-43-7 ]
copper(II) oxide [ No CAS ]
{Cugl₂}*CuCl₂*2H₂O [ No CAS ]

Reference： [1]Spisy prirodovedeckou Fak. Masarykovy Univ. (tschech.) Nr. 115 (1929) 12/16,
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 90, page 1633 - 1635

55
samarium(III) carbonate [ No CAS ]
[ 6000-43-7 ]
Sm⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Sm(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

56
yttrium(III) carbonate [ No CAS ]
[ 6000-43-7 ]
Y⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Y(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

57
dysprosium(III) carbonate [ No CAS ]
[ 6000-43-7 ]
Dy⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Dy(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

58
cerium (III) carbonate [ No CAS ]
[ 6000-43-7 ]
Ce⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Ce(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

59
praseodymium carbonate [ No CAS ]
[ 6000-43-7 ]
Pr⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Pr(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

60
lanthanum(III) carbonate [ No CAS ]
[ 6000-43-7 ]
La⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=La(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

61
neodymium carbonate [ No CAS ]
[ 6000-43-7 ]
Nd⁽³⁺⁾*3H₃NCH₂COO*3Cl^(1-)*3H₂O=Nd(C₂H₅NO₂)3Cl₃*3H₂O [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1970,vol. 32,p. 3277 - 3281
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D1, 3.1.1.1, page 103 - 105

62
[ 6000-43-7 ]
[ 12775-96-1 ]
[ 107-15-3 ]
[ 188638-27-9 ]

Reference： [1]Polyhedron,1997,vol. 16,p. 1723 - 1729

63
[ 1186048-83-8 ]
[ 6000-43-7 ]
[ 17585-69-2 ]
[ 6003-05-0 ]
[ 17694-98-3 ]
[ 7776-34-3 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 7171 - 7176

64
[ 32315-10-9 ]
[ 1159822-52-2 ]
[ 6000-43-7 ]
[ 1240282-72-7 ]

Yield	Reaction Conditions	Operation in experiment
76%		Method 8; 2-(3-(6-(5-(N-tert-butylsulfamoyl)pyridin-3-yl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)ureido)acetic acid5-(2-amino-[ 1 ,2,4]triazolo[ 1 ,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide (250 mg, 0.14 mmol) was suspended in tetrahydrofuran:pyridine (5 mL, 5:1) and cooled to 00C. Triphosgene (215 mg, 0.72 mmol) was added in one portion and the reaction mixture heated at 35 0C for 2 hours. After this time the solvent was decanted and the resultant semi-solid dissolved in DMF:pyridine (2 mL, 10: 1). <strong>[6000-43-7]Glycine hydrochloride</strong> (270 mg, 3.6 mmmol) was added in one portion and the reaction mixture heated for 18 hours at 65 0C. After this time the solvent was removed in vacuo and hydrochloride acid (IM, aqueous solution) was added to the resultant oil to afford a brown solid. The title compound was collected by filtration (244 mg, 0.55 mmol, 76 %). No further purification was required. LCMS (method A) (M+H+) 448, Rt = 2.07 min

Reference： [1]Patent: WO2010/92015,2010,A1 .Location in patent: Page/Page column 59

65
C₁₉H₂₂N₂O₇ [ No CAS ]
[ 6000-43-7 ]
[ 1246961-65-8 ]

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2021 - 2026

66
[ 6000-43-7 ]
[ 68-12-2 ]
N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium diperchlorate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2702 - 2714
[2]Synthesis,2011,p. 887 - 894

67
[ 1334715-68-2 ]
[ 6000-43-7 ]
[ 17585-69-2 ]
[ 7776-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 110℃; for 20h;	General procedure: Compounds 1-3 (each 1 mg) were hydrolyzed in HCl (6 N; 1 mL) for 20 h at 110 °C. The solution was then evaporated to dryness and redissolved in H2O (250 muL). A 1percent (w/v) solution (100 muL) of l-FDAA in acetone was added to an aliquot (50 muL) of the acid hydrolyzate solution. After addition of NaHCO3 solution (1 N; 20 muL) the mixture was incubated at 45 °C for 1 h. The reaction was then quenched by addition of HCl (2 N, 10 muL). Analyses of the FDAA-derivatized hydrolyzates of compounds 1-3 and standard FDAA-derivatized amino acids were carried out by HPLC (Waters 600E; solvents: A. water+0.2percent TFA, B. MeCN; linear gradient: 0-5 min, 15percent B; 5-50 min, 15-45percent B; 50-55 min, 45percent B; temperature, 30 °C; flow rate, 1 mL/min; UV detection at lambdamax 340 nm). Retention times (min) of the amino acids derivatives were as follows: l/d-Ala, tR 29.6/34.4 min; l/d-Pro, tR 30.6/32.3 min; l/d-Phe, tR 40.8/51.2 min. The derivatized hydrolyzates of 1-3 showed peaks designated as l-Ala, l-Pro, and l-Phe. All amino acids of these cyclopeptides were established as l-configuration.

Reference： [1]Tetrahedron,2011,vol. 67,p. 7085 - 7089

68
[ 1185-53-1 ]
[ 6000-43-7 ]

Yield	Reaction Conditions	Operation in experiment
		Elution Buffer: 0.1 M Glycine-HCl, pH 2.6 Neutralization buffer: 1 M Tris-HCl, pH 9.0

Reference： [1]Patent: US2011/243942,2011,A1

69
[ 6000-43-7 ]
[ 1122-91-4 ]
[ 1727-09-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362

70
[ 71-23-8 ]
[ 6000-43-7 ]
[ 13049-01-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride; at 20 - 70℃; for 15h;Inert atmosphere;	Preparation Example 19Propyl 2-aminoacetate hydrochlorideTo a solution of glycine hydrochloride 46 (4.5 g, 40. 3 mmol) in «-propanol (60 mL) was slowly added SOCl2 (13.5 mL) at room temperature. The reaction mixture was stirred at 70 C for 15 h. After cooling to room temperature, the mixture was evaporated under vacuum to provide the titled compound (6.1 g, 98 %) as a white solid. MH+ 118.Subsequent esterification under acidic conditions yields ester 25 in 92% yield.

Reference： [1]Patent: WO2011/159067,2011,A2 .Location in patent: Page/Page column 59-60

71
[ 6000-43-7 ]
[ 68-12-2 ]
[(2Z)-3-(dimethylamino)-2-[(E)-[(dimethylamino)methylidene]amino]prop-2-en-1-ylidene]dimethylazanium hexafluoro-λ5-phosphanuide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		Example 12: 3-hydroxy-l-(2-methylpyrimidin-5-yl)-4-[4^ropan-2-yl)phenyl] carbonyl}-5-[4-(trifluoromethoxy)phenyl]-2,5-dihydro-lH-pyrrol-2-onea) [(2Z)-3-(dimethylamino)-2-[(iT)-[(&y li dene] dimethyl azanium ; hexafluoro-lambda5 -pho sphanuide; To dimethylformamide (50 ml) was added dropwise POCI3 (23.4 mL; 250 mmol; 3 eq) at 10C. The solution was stirred at 15C for 1 hour, then glycine hydrochloride (9.3 g; 83 mmol; 1 eq) was slowly added. After 4 hours at 80C, the mixture was poured into cold water (120 mL) and the resulting mixture was stirred 15 minutes at 0C. An aqueous solution of HPF6 (24 mL) was then added and the resulting precipitate was filtered, washed with EtOH ( 120 mL) and dried under high vacuum . The title compound, [(2Z)-3-(dimethylamino)-2-[(JE)-[(dimethylamino)methylidene]amino]prop- 2-en-l-ylidene]dimethylazanium;hexafluoro- 5-phosphanuide was obtained in 78 % yield as a beige powder.1H-NMR (DMSO-de): delta (ppm) = 3.21 (s, 9 H), 3.26 (s, 3H), 3.3 (s, 6H), 7.72 (s, 1H), 8.08 (d, 1H), 10.86 (d, 1H)

Reference： [1]Patent: WO2012/93174,2012,A1 .Location in patent: Page/Page column 56

72
[ 28920-43-6 ]
[ 6000-43-7 ]
[ 29022-11-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 10575 - 10582

73
[ 6000-43-7 ]
[ 68-12-2 ]
[(E)-3-dimethylamino-2-(dimethylaminomethyleneamino)allylidene]dimethylammonium hexafluorophosphate [ No CAS ]

Reference： [1]Organic Process Research and Development,2006,vol. 10,p. 70 - 77

74
Zr⁽⁴⁺⁾*0.2C₆H₅O₃P^(2-)*1.8C₆H₅O₆PS^(2-)*2.3H₂O [ No CAS ]
[ 6000-43-7 ]
Zr⁽⁴⁺⁾*0.2C₆H₅O₃P^(2-)*1.8C₆H₅O₆PS^(2-)*H₂O*C₂H₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 20℃; for 96h;	General procedure: For the intercalations of aromatic amines and diamines, a five fold molar excess of the corresponding amine was hydrothermally treated in water (9mL) with ZrSPhP 2H2O at 130C for 20h .Imidazole and pyridine were intercalated by stirring a suspension of ZrSPhP 2H2O with a five foldmolar excess of the corresponding heterocycle in the water/ethanol mixture(1:1) at 50 C for 4 days. 4,4?-Bipyridine was intercalated by both abovementioned methods (at 130 C and 50 C). Poly(ethyleneimine)was intercalated analogously at 50 C using 50% aqueous solution of poly(ethyleneimine)(2mL)added to asuspension of ZrSPhP 2H2O in 20 mL of a water/ethanol mixture(1:1). Amino acids were intercalated by stirring a suspension of ZrSPhP 2H2O with a five fold molar excess of the corresponding amino acid in the water-ethanol mixture(1:1)at room temperature for 4 days.The resulting mixtures were centrifuged, the separated solid interca-lates were washed with the water-ethanol mixture and dried at ambient conditions.Elemental analysiscalcd./foundforthefollowingselectedintercalates: p-Toluidine-C,38.96/33.0970.21;H, 3.75/3.6670.09;N,3.32/4.5270.06;S,7.61/7.9870.10%forZr(C6H5PO3)0.2(HO3SC6H4PO3)1.8 1.8C7H7NH2 H2O. 1,8-Diaminonaph-thalene -C,34.71/33.0870.12;H,2.91/3.6470.04;N,3.24/3.0370.02;S,8.34/7.2270.09% forZr(C6H5PO3)0.2(HO3SC6H4PO3)1.8 0.8C10H10N2 2H2O.1-Aminopyrene-C,48.51/47.5770.07;H,3.22/3.8970.04;N,2.36/2.4670.10;S,6.48/5.7570.29%forZr(C6H5PO3)0.2(HO3SC6H4PO3)1.8 1.5C16H11NH2O.

Reference： [1]Journal of Solid State Chemistry,2013,vol. 208,p. 58 - 64

75
[ 3782-70-5 ]
[ 6000-43-7 ]
[ 1148144-77-7 ]

Reference： [1]Medicinal Chemistry Research,2014,vol. 23,p. 2476 - 2485

76
C₂₀H₁₈N₆O₃S [ No CAS ]
[ 6000-43-7 ]
methyl 2-(3-(2-(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-ylthio)acetamido)propanamido)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.19 g	With triethylamine; In ethyl acetate; at -5 - 25℃; for 48h;	General procedure: To a cold solution (-5C) of hydrazide 14a-c(1.0 mmol) in AcOH (6 mL), 1 N HCl (3 mL), and water (25 mL)was added a solution of NaNO2 (0.34 g, 5.0 mmol) in cold water (3 mL). After stirring at -5C for 1 h. A thick precipitate was formed. The reaction mixture was extracted in cold ethyl acetate (30 mL), washed with cold 3% NaHCO3, H2O and finally dried (Na2SO4). A solution of amino acid esters hydrochloride (1.0 mmol) in ethyl acetate (20 mL) containing 0.2 mL of triethylamine was added to the ethyl acetate azide solution 15a-c. The mixture was kept at -5C for 24 h, then at 25C for another 24 h, followed by washing with 0.5 N HCl,water, 3% solution of NaHCO3 and finally d ried ( Na2SO4).The solution was evaporated to dryness, and the residue was recrystallized from petroleum ether-ethyl acetate to give the corresponding quinazoline dipeptide 16a-c.

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 675 - 694

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[ 6000-43-7 ]
[ 156691-57-5 ]
[ 1629871-51-7 ]

Yield	Reaction Conditions	Operation in experiment
89.2 mg	With triethylamine; In tetrahydrofuran;Reflux;	General procedure: Into a round-bottom flask, the azide derivative 1 (1 mmol, 1 equiv)was introduced in THF (1 mL) at r.t. Ph3P (2 mmol, 2 equiv) andCS2 (10 mmol, 10 equiv) were added and the solution was refluxeduntil formation of the isothiocyanate, as monitored by TLC. Themixture was concentrated under reduced pressure, after which anamino acid methyl ester (1 mmol, 1 equiv) and Et3N (8 mmol, 8equiv) were added in THF (1 mL). The solution was refluxed untilthe transformation of the isothiocyanate, as monitored by TLC. Themixture was concentrated under reduced pressure, then purified bycolumn chromatography on silica gel.