[ CAS No. 7326-73-0 ] {[proInfo.proName]}

Name: 7326-73-0|3-(N,N-Dimethylsulfamoyl)benzoic acid|97%
Brand: Ambeed
SKU: A312536
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Quality Control of [ 7326-73-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 7326-73-0 ]

Product Details of [ 7326-73-0 ]

CAS No. :	7326-73-0	MDL No. :	MFCD02708231
Formula :	C₉H₁₁NO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZYUAOEFMKIYOPZ-UHFFFAOYSA-N
M.W :	229.25	Pubchem ID :	4985762
Synonyms :

Calculated chemistry of [ 7326-73-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.2
TPSA :	83.06 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) :	-7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.18
Log Po/w (XLOGP3) :	0.39
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	0.6
Log Po/w (SILICOS-IT) :	-0.32
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.61
Solubility :	5.69 mg/ml ; 0.0248 mol/l
Class :	Very soluble
Log S (Ali) :	-1.7
Solubility :	4.57 mg/ml ; 0.0199 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.81
Solubility :	3.51 mg/ml ; 0.0153 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 7326-73-0 ]

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

Application In Synthesis of [ 7326-73-0 ]

* 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 [ 7326-73-0 ]
Downstream synthetic route of [ 7326-73-0 ]

[ 7326-73-0 ] Synthesis Path-Upstream 1~1

1
[ 4025-64-3 ]
[ 124-40-3 ]
[ 7326-73-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: for 0.5 h; Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane; water	A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in TΗF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10percent HCl and extracted with EtOAc. The organics were washed with NaCl(sat) and then dried with Na2SO4(s). The organics were then removed under reduced pressure to give 1.80 g, 65percent; m/z 229.
65%	Stage #1: for 0.5 h; Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane; water	A solution of 3-(chlorosulfonyl)benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10percent HC1 and extracted with EtOAc. The organics were washed with NaCl(_Sat) and then dried with Na2S04(_S). The organics were then removed under reduced pressure to give 1.80 g, 65percent; m/z 229.
65%	for 0.5 h;	Method 25; 3-[(Dimethylamino)sulfonyr\|benzoic acid; A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10percent HCl and extracted with EtOAc. The organics were washed with νaCl(sat) and dried with Na₂SO₄(S). The organics were then removed under reduced pressure to give 1.80 g, 65percent; m/z 229.

65%

at 20℃; for 0.333333 h;

Method 128; 5 3 - \\( Dimethylamino)sulfonyll benzoic acid; A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10percent HCl and extracted with EtOAc. The organics were washed with NaCl (sat) and then dried with Na₂SO₄ (s). The organics were then removed under 10 reduced pressure to give 1.80 g, 65percent; m/z 229.

Reference： [1] ChemMedChem, 2015, vol. 10, # 9, p. 1548 - 1558
[2] Patent: WO2006/24834, 2006, A1, . Location in patent: Page/Page column 82
[3] Patent: WO2006/24836, 2006, A1, . Location in patent: Page/Page column 30
[4] Patent: WO2007/71963, 2007, A2, . Location in patent: Page/Page column 50
[5] Patent: WO2006/40568, 2006, A1, . Location in patent: Page/Page column 82
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 15, p. 6146 - 6155
[7] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1807 - 1816
[8] Tetrahedron, 2004, vol. 60, # 17, p. 3755 - 3762
[9] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4552 - 4557

[ 7326-73-0 ] Synthesis Path-Downstream 1~41

1
[ 64-17-5 ]
[ 7326-73-0 ]
[ 83112-39-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816

2
[ 4025-64-3 ]
[ 124-40-3 ]
[ 7326-73-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in TEtaF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10% HCl and extracted with EtOAc. The organics were washed with NaCl(sat) and then dried with Na2SO4(s). The organics were then removed under reduced pressure to give 1.80 g, 65%; m/z 229.
65%		A solution of 3-(chlorosulfonyl)benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10% HC1 and extracted with EtOAc. The organics were washed with NaCl(Sat) and then dried with Na2S04(S). The organics were then removed under reduced pressure to give 1.80 g, 65%; m/z 229.
65%	In tetrahydrofuran; dichloromethane; for 0.5h;	Method 25; 3-[(Dimethylamino)sulfonyr\|benzoic acid; A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10% HCl and extracted with EtOAc. The organics were washed with nuaCl(sat) and dried with Na2SO4(S). The organics were then removed under reduced pressure to give 1.80 g, 65%; m/z 229.

65%	In tetrahydrofuran; dichloromethane; at 20℃; for 0.333333h;	Method 128; 5 3 - ( Dimethylamino)sulfonyll benzoic acid; A solution of 3-(chlorosulfonyl) benzoic acid (2.60 g, 12 mmol) in DCM (20 ml) was treated with dimethylamine (2.0 M in THF, 20 ml, 40 mmol, 3.3 equiv). After 30 min, the reaction was quenched with 10% HCl and extracted with EtOAc. The organics were washed with NaCl (sat) and then dried with Na2SO4 (s). The organics were then removed under 10 reduced pressure to give 1.80 g, 65%; m/z 229.
2.93 g	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 0 - 5℃; for 2h;	Preparation of 3-(N,N-dimethylsulfamoyl)benzoic Acid, Intermediate 13.0 To a round-bottom flask was added dimethylamine (2.0M in THF, 9.1 mL, 18.2 mmol) and DCM (40 mL). The solution was cooled to 0 C. and DIPEA (7.88 mL, 45.3 mmol) was added followed by 3-(chlorosulfonyl)benzoic acid (4.0 g, 18.1 mmol) in portions maintaining the temperature <5 C. The reaction was stirred at 0 C. for 2 h then 1N NaOH (50 mL) was added and the phases were separated. The organics were washed with 1N NaOH (2*50 mL) and the aqueous extracts were collected and acidified with conc. HCl to pH 2. The resulting precipitate was collected by filtration and dried under reduced pressure to give the desired product (2.93 g). 1H NMR (500 MHz, DMSO-d6) delta ppm 13.55 (br s, 1H), 8.23-8.29 (m, 1H), 8.18-8.22 (m, 1H), 7.95-8.06 (m, 1H), 7.74-7.85 (m, 1H), 2.63 (s, 6H). LCMS-ESI (POS.). m/z: 230.2 (M+H)+.

Reference： [1]ChemMedChem,2015,vol. 10,p. 1548 - 1558
[2]Patent: WO2006/24834,2006,A1 .Location in patent: Page/Page column 82
[3]Patent: WO2006/24836,2006,A1 .Location in patent: Page/Page column 30
[4]Patent: WO2007/71963,2007,A2 .Location in patent: Page/Page column 50
[5]Patent: WO2006/40568,2006,A1 .Location in patent: Page/Page column 82
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 6146 - 6155
[7]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816
[8]Tetrahedron,2004,vol. 60,p. 3755 - 3762
[9]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4552 - 4557
[10]Patent: US2019/77793,2019,A1 .Location in patent: Paragraph 0235-0236

Yield	Reaction Conditions	Operation in experiment
90.6%	In water; ethyl acetate; at 0℃; for 0.5h;	General procedure: To a saturated solution of 3-chloro sulfonyl benzoic acid (8 mmol) in ethyl acetate (4 mL) was added cold concentrated ammonia or methylamine aqueous solution. After stirring for 30 min at 0 deg C., the mixture was neutralized with a solution of HCl in dioxane (4M) and extracted with ethyl acetate. The organic phase was concentrated under reduced pressure to give a solid which was recrystallized from acetonitrile to give desired compound.3-Methylsulfamoyl-benzoic Acid[0236][0237]white solid, yield 54%, 1HNMR (300 MHz, DMSO-d6) delta 8.30 (s, 1H, Ar-H), 8.17 (d, J=7.8 Hz, 1H, Ar-H), 7.99 (d, J=8.1 Hz, 1H, Ar-H), 7.75 (t, J=7.8 Hz, 1H, Ar-H), 7.62 (d, J=4.8 Hz, 1H, NH), 2.4 (s, 3H, Me).

4
[ 7326-73-0 ]
[ 188674-88-6 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 3755 - 3762
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 6146 - 6155

5
[ 7326-73-0 ]
2-(3-dimethylsulfamoyl-benzoylamino)-4-methyl-pentanoic acid [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 3755 - 3762

6
[ 65-85-0 ]
/PPFKE₁₂₃-1965/ [ No CAS ]
[ 7326-73-0 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 3755 - 3762

7
[ 7326-73-0 ]
[ 96134-79-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816
[2]Patent: WO2013/25805,2013,A1
[3]Journal of Medicinal Chemistry,2013,vol. 56,p. 9496 - 9508
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4552 - 4557

8
[ 7326-73-0 ]
[ 96134-49-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816

9
[ 7326-73-0 ]
[ 96134-50-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816

10
[ 7326-73-0 ]
[ 96134-51-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816

11
[ 7326-73-0 ]
[ 96134-52-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1807 - 1816

12
[ 7326-73-0 ]
[ 119-32-4 ]
[ 878756-98-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 50℃; for 12h;	A solution of 3-[(dimethylamino)sulfonyl]benzoic acid (Method 14) (1.00 g, 4.36mmol), 4-methyl-3-nitroaniline (664 mg, 4.36 mmol) and diisopropylethylamine (2.3 ml, 13.08 mmol, 3.0 equiv) in 10 ml of DMF was treated with HATU (2.00 g, 5.23 mmol, 1.2 equiv). The reaction was stirred at 50 C for 12 hours. The reaction was quenched with FfcO and extracted with EtOAc. A precipitate resulted during this process, thus the solid was collected by vacuum filtration to give 1.14 g, 72% of the desired product; m/z 365.

Reference： [1]Patent: WO2006/24836,2006,A1 .Location in patent: Page/Page column 30

13
[ 67-56-1 ]
[ 7326-73-0 ]
[ 823833-29-0 ]

Yield	Reaction Conditions	Operation in experiment
125 mg	With sulfuric acid; at 70℃;	3-(A/,/V-Dimethylsulfamoyl)benzoic acid (200 mg, 0.872 mmol) was refluxed overnight in the presence of concentrated sulfuric acid (5.64 mg, 0.044 mmol) in methanol (10 mL) at 70 C. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography affording the title compound (125 mg). 1H NMR (400 MHz, CDCI3): delta 8.42 (s, 1 H), 8.27 (d, 1 H, J = 8.0 Hz), 7.97 (d, 1 H, J = 7.2 Hz), 7.65 (t, 1 H, J = 8.0 Hz), 3.96 (s, 3H), 2.74 (s, 6H). ESI-MS: 244.0 [M+H]+.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9496 - 9508
[2]Patent: WO2013/25805,2013,A1 .Location in patent: Page/Page column 90
[3]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4552 - 4557

14
[ 7326-73-0 ]
[ 1423715-15-4 ]

Reference： [1]Patent: WO2013/25805,2013,A1

15
[ 7326-73-0 ]
[ 930688-81-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6146 - 6155

16
[ 7326-73-0 ]
[ 724440-74-8 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6146 - 6155

17
[ 7326-73-0 ]
(Z)-3-(2-(1-(5-chloro-2-hydroxyphenyl)ethylidene)hydrazinecarbonyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9496 - 9508

18
[ 7326-73-0 ]
3-(hydroxymethyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1548 - 1558

19
[ 7326-73-0 ]
3-formyl-N, N-dimethyl-benzenesulfonamide [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1548 - 1558

20
[ 7326-73-0 ]
[ 1421506-08-2 ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1548 - 1558

21
[ 7326-73-0 ]
(E)-3-(2-(7-hydroxy-2,3-dihydro-1H-inden-1-ylidene)hydrazinecarbonyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4552 - 4557

22
[ 7326-73-0 ]
(E)-3-(2-(4-chloro-7-hydroxy-2,3-dihydro-1H-inden-1-ylidene)hydrazinecarbonyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4552 - 4557

23
[ 7326-73-0 ]
C₁₄H₁₈N₄O₃ [ No CAS ]
(E)-3-(N,N-dimethylsulfamoyl)-N-(1-(3-hydroxypropyl)-5-(3-oxomorpholino)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 1h;	General procedure: In a glass RBF equipped with a Teflon-coated magnetic stirrer was dissolved 4- methyl-3-trifluoromethyl-benzoic acid (1 eq.), HBTU (1.1 eq.) and ethyl-diisopropyl-amine (3 eq.) in acetonitrile (0.12 M). To this was then added Intermediate 1-OH (1 eq.) as a solution (0.12 M) in 9:1 (v/v) DMF: MeCN and the resulting yellow solution was allowed to stir at RT for 1 h. The crude reaction mixture was directly subjected to purification by way of column chromatography (Si02, gradient elution, CH2C12 - 9:1 (v/v) CH2C12: MeOH). The product thus obtained can then be triturated in methanol and ether to furnish the title compound as a white solid (22% yield). Prepared in an analogous fashion to Example 9, but using 3-dimethylsulfamoyl- benzoic acid (1.2 eq.) in place of 4-methyl-3-trifluoromethyl-benzoic acid and TBTU (1.2 eq.) in place of HBTU (25% yield). ESI: M+1: 502. ?H NMR (300 MHz, DMSO-d6) oe 8.59 - 8.50 (m, 2H), 7.95 - 7.85 (m, 1H), 7.77 (t, J = 7.9 Hz, 1H), 7.63 - 7.47 (m, 2H), 7.28 (dd, J = 8.6, 2.0 Hz, 1H), 4.34 (t, J= 6.8 Hz, 2H), 4.23 (s, 2H), 4.06-3.96 (m, 2H), 3.75 (t, J= 5.1 Hz, 2H), 3.48 (t, J = 6.2 Hz, 2H), 2.65 (s, 6H), 1.97 (t, J= 6.5 Hz, 2H).

Reference： [1]Patent: WO2017/49068,2017,A1 .Location in patent: Paragraph 00353; 00355

24
[ 7326-73-0 ]
(3-(N,N-dimethylsulfamoyl)benzoyl)-D-proline [ No CAS ]

Reference： [1]Patent: US2019/77793,2019,A1

25
[ 7326-73-0 ]
D-proline benzyl ester hydrochloride [ No CAS ]
benzyl (3-(N,N-dimethylsulfamoyl)benzoyl)-D-prolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 23℃; for 5h;	Step 1: Preparation of Benzyl (3-(N,N-dimethylsulfamoyl)benzoyl)-D-prolinate To a 250 mL round-bottom flask was added <strong>[7326-73-0]3-(N,N-dimethylsulfamoyl)benzoic acid</strong> (1.8 g, 7.9 mmol), TBTU (2.5 g, 7.9 mmol), (R)-benzyl pyrrolidine-2-carboxylate hydrochloride (1.9 g, 7.9 mmol) and dichloromethane (40 mL). After cooling to 0 C., DIPEA (4.1 mL, 23.6 mmol) was added. The reaction was allowed to warm to 23 C. and stirred for an additional 5 h then 1N HCl (20 mL) was added. The organics were separated and concentrated under reduced pressure and the crude residue was purified using silica gel chromatography (50-100% EtOAc/heptanes) to obtain the desired product as a vicious oil. LCMS-ESI (POS.). m/z: 417.2 (M+H)+.

Reference： [1]Patent: US2019/77793,2019,A1 .Location in patent: Paragraph 0239

26
[ 7326-73-0 ]
2-amino-N-[4-(2-bromophenyl)thiazol-2-yl]acetamide trifluoroacetate [ No CAS ]
N-[2-[[4-(2-bromophenyl)thiazol-2-yl]amino]-2-oxoethyl]-3-(dimethylsulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (96.82 mg, 422.33 pmol) in DMF (3.0 mL) were added HATU (401 .46 mg, 1 .06 mmol) and DIEA (227.43 mg, 1 .76 mmol, 306.51 pL) and the mixture was stirred at 30 C for 30 min. Then intermediate i-35b (150 mg, 351 .94 pmol) was added. The mixture was stirred at 30 C for 16 hrs, then poured into H2O (30.0 mL) and extracted with EtOAc (5.0 mL3). The combined organic extracts were washed with H2O (5.0 mL2) and brine (5.0 mL), then dried over Na2SC>4, filtered and concentrated under vacuum. The residue was purified by Prep-HPLC (column: Phenomenex Synergi C1 8 1502510 pm; mobile phase: [water(0.1 %TFA)-ACN];B%: 42%-72%, 9 min) and lyophilized to give compound 18 as a light yellow solid. 1 H NMR (400 MHz, DMSO-de) d = 12.51 (s, 1 H), 9.34-9.31 (m, 1 H), 8.27-8.23 (m, 2H), 7.94 (d, J=8.0 Hz, 1 H), 7.83-7.81 (m, 1 H), 7.75-7.69 (m, 2H), 7.54 (s, 1 H), 7.48-7.46 (m, 1 H), 7.32-7.30 (m, 1 H), 4.24 (d, J=5.6 Hz, 2H), 2.66 (s, 6H) ppm LCMS (ESI) m/z: [M+H]+=525.0.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 115-116

27
[ 7326-73-0 ]
2-amino-N-[4-(3-bromophenyl)thiazol-2-yl]acetamide trifluoroacetate [ No CAS ]
N-[2-[[4-(3-bromophenyl)thiazol-2-yl]amino]-2-oxoethyl]-3-(dimethylsulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (96.82 mg, 422.33 pmol) in DMF (3.0 ml_) were added HATU (401 .46 mg, 1 .06 mmol) and DIEA (227.43 mg, 1 .76 mmol, 306.51 pL) and the mixture was stirred at 30 C for 30 min. Then intermediate i-36b (150 mg, 351 .94 pmol) was added. The mixture was stirred at 30 C for 16 hrs then poured into FEO (30.0 ml_) and extracted with EtOAc (5.0 mL3). The combined organic extracts were washed with H2O (5.0 ml_2) and brine (5 ml_), then dried over Na2SC>4, filtered and concentrated under vacuum. The residue was purified by Pre-HPLC (column: Phenomenex Synergi C18 1502510 pm; mobile phase: [water(0.1 %TFA)-ACN];B%: 42%-72%,9 min) and lyophilized to give compound 7 as a pink solid. 1H NMR (400 MHz, DMSO-de) d = 12.51 (s, 1 H), 9.33-9.30 (m, 1 H), 8.27-8.23 (m, 2H), 8.1 1 (s, 1 H), 7.94- 7.91 (m, 2H), 7.82-7.80 (m, 2H), 7.43-7.42 (m, 1 H), 7.41 -7.40 (m, 1 H), 4.24 (d, J=5.6 Hz, 2H), 2.66 (s, 6H) ppm LCMS (ESI) m/z: [M+H]+=523.2.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 117

28
[ 7326-73-0 ]
(S)-(9H-fluoren-9-yl)methyl (2-amino-3-oxo-3-((4-phenylthiazol-2-yl)amino)propyl)carbamate trifluoroacetate [ No CAS ]
(S)-(9H-fluoren-9-yl)methyl (2-(3-(N,N-dimethylsulfamoyl)benzamido)-3-oxo-3-((4-phenylthiazol-2-yl)amino)propyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 12h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (38.30 mg, 167.06 gmol) in DCM (1 .0 ml_) were added HATU (69.87 mg, 183.76 gmol), DIEA (64.77 mg, 501 .18 gmol, 87.30 gl_) and intermediate i- 45b (100 mg, 167.06 gmol). The reaction mixture was stirred at 20 C for 12 hours and then poured into water (2.0 ml_). The solution was extracted with EtOAc (2.0 ml_ * 3). The combined organic extracts were washed with brine (5.0 ml_), dried over Na2SC>4 and filtered. The filtrate was concentrated to give a residue. The residue was purified by column chromatography (S1O2. PE/EA=50/1 -1 /1 ) to give intermediate i-45c as a white solid. LCMS (ESI) m/z: [M+H]+ = 696.0 Chiral HPLC: OJ-3-MeOH(DEA)-60-7MIN-3ML-35T, 5.276min.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 125

29
[ 7326-73-0 ]
2-amino-N-(4-(2-cyanophenyl)thiazol-2-yl)acetamide trifluoroacetate [ No CAS ]
N-(2-((4-(2-cyanophenyl)thiazol-2-yl)amino)-2-oxoethyl)-3-(N,N-dimethylsulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 30℃; for 12h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (81 .41 mg, 355.13 pmol) in DCM (2.0 ml_) were added HATU (162.04 mg, 426.15 pmol), DIEA (183.59 mg, 1 .42 mmol) and intermediate i-47b (1 10.0 mg, 355.13 pmol). The reaction mixture was stirred at 30 C for 12 hr. The reaction mixture was poured into water (5.0 ml_). Then the solution was extracted with EtOAc (5.0 ml_3). The combined organic extracts were washed with brine (10.0 ml_), dried over Na2SC>4 and filtered. The filtrate was concentrated to give a residue. The residue was purified by Pre-HPLC (column: Phenomenex Synergi C18 1 5025*10 pm; mobile phase: [water (0.225%FA)-ACN]; B%: 37%-57%, 7 min) and lyophilized to give compound 27 as a white solid. 1 H NMR (400MHz, DMSO-de) d = 12.43 (br s, 1 H), 9.32 (m, 1 H), 8.26-8.25 (m, 2H), 7.97-7.92 (m, 3H), 7.80-7.79 (m, 3H), 7.56 (m, 1 H), 4.26 (d, J= 5.6 Hz, 2H), 2.65 (s, 6H) ppm LCMS (ESI) m/z: [M+H] + = 470.2

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 127

30
[ 7326-73-0 ]
2-amino-N-(6-phenyl-2-pyridyl)acetamide trifluoroacetate [ No CAS ]
[ 76-05-1 ]
3-(dimethylsulfamoyl)-N-[2-oxo-2-[(6-phenyl-2-pyridyl)amino]ethyl]benzamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (36.58 mg, 159.54 pmol), HATU (60.66 mg, 159.54 pmol) and DIPEA (74.98 mg, 580.16 pmol) in DCM (1 .0 mL) was added Intermediate i-55b (50.0 mg, 145.04 pmol) and the mixture was stirred at 25 C for 2 hr. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Phenomenex Synergi C18 1502510 pm; mobile phase: [water (0.1 %TFA)-ACN]; B%: 35%-65%, 9 min) and lyophilized to give compound 41 (TFA salt) as a white solid. 1 H NMR (400MHz, DMSO-de) d 1 0.68 (s, 1 H), 9.24-9.21 (m, 1 H), 8.27-8.26 (m, 2H), 8.10-8.08 (m, 2H), 8.02 (d, J= 8.0 Hz, 1 H), 7.96-7.93 (m, 1 H), 7.90-7.88 (m, 1 H), 7.82-7.78 (m, 1 H), 7.69 (d, J= 8.0 Hz, 1 H), 7.51 -7.46 (m, 3H), 4.23 (d, J= 6.0 Hz, 2H), 2.68-2.66 (m, 6H) ppm. LCMS (ESI) m/z: [M+H]+ = 439.0.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 139-140

31
[ 7326-73-0 ]
2-amino-N-[4-(3-cyanophenyl)thiazol-2-yl]acetamide trifluoroacetate [ No CAS ]
N-[2-[[4-(3-cyanophenyl)thiazol-2-yl]amino]-2-oxoethyl]-3-(dimethylsulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 25℃; for 12h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (75.74 mg, 330.36 pmol) in DCM (2.0 mL) were added HATU (138.17 mg, 363.40 pmol), DIEA (170.79 mg, 1 .32 mmol, 230.17 pL) and intermediate F (123.0 mg, 330.36 pmol. The mixture was stirred at 25 C for 12 hr. The reaction mixture was diluted with water (10.0 mL) and extracted with EtOAc (30.0 mL * 3). The combined organic extracts were washed with brine (20.0 mL * 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (TFA condition; column: Phenomenex Synergi C18 1502510 pm; mobile phase: [water (0.1 %TFA)-ACN]; B%: 35%-65%, 9 min) and lyophilized to give compound 8 as a white solid. 1HNMR (400MHz, DMSO-de) d 12.53 (s, 1 H), 9.34-9.31 (m, 1 H), 8.33 (s, 1 H), 8.26-8.22 (m, 3H), 7.94 (d, J=8.0 Hz,1 H), 7.88 (s, 1 H), 7.82-7.78 (m, 2H), 7.68-7.64 (m, 1 H), 4.24 (d, J= 5.6 Hz, 2H), 2.65 (s, 6H). LCMS (ESI) m/z: [M+H]+ = 470.0.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 129-130

32
[ 7326-73-0 ]
2-amino-N-[4-(4-cyanophenyl)thiazol-2-yl]acetamide trifluoroacetate [ No CAS ]
N-[2-[[4-(4-cyanophenyl)thiazol-2-yl]amino]-2-oxoethyl]-3-(dimethylsulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 25℃; for 24h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (244.08 mg, 1 .06 mmol) in DCM (5.0 ml_) were added HATU (404.82 mg, 1 .06 mmol), DIEA (500.36 mg, 3.87 mmol, 674.34 pL) and intermediate i-51 c (250.0 mg, 967.87 pmol. The mixture was stirred at 25 C for 24 hr. The reaction mixture was diluted with water (1 0.0 ml_) and extracted with EtOAc (15.0 ml_ * 3). The combined organic extracts were washed with brine (1 0.0 mL2), dried over Na2SC>4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (TFA condition ; column: Phenomenex Synergi C18 1 5025*10 pm; mobile phase: [water (0.1 %TFA)-ACN];B%: 45%-75%,9 min) and lyophilized to give intermediate i-51 d as a white solid. 1 H NMR (400MHz, DMSO-de) d 12.27 (s, 1 H), 9.33-9.30(m, 1 H), 8.26-8.23(m, 2H), 8.08 (d, J=8.4 Hz, 2H), 7.95 -7.89 (m, 4H), 7.82-7.78 (m, 1 H), 4.24 (d, J= 5.6 Hz, 2H), 2.65 (s, 6H) ppm. LCMS (ESI) m/z: [M+H]+=469.2.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 132

33
[ 7326-73-0 ]
(2S)-2-amino-4-methylsulfanyl-N-(4-phenylthiazol-2-yl)butanamide [ No CAS ]
(S)-3-(N,N-dimethylsulfamoyl)-N-(4-(methylthio)-1-oxo-1-((4-phenylthiazol-2-yl)amino)butan-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; at 28℃; for 2h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (59.66 mg, 260.22 gmol) in DCM (2 ml_) was added EEDQ (96.52 mg, 390.33 gmol) and then (2S)-2-amino-4-methylsulfanyl-N-(4-phenylthiazol-2- yl)butanamide (80 mg, 260.22 gmol) was added. The mixture was stirred at 28C for 2 hr. The reaction mixture was diluted with EtOAc (150 ml_). The organic layer was washed with brine (50 ml_), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=50/1 to 1 :1 ) and lyophilized to give compound 24 as a white solid. 1 H NMR (400 MHz, DMSO-d6) d 12.55 (s, 1 H) , 9.10 (d, J= 6.8 Hz, 1 H), 8.28-8.26 (m, 2H), 7.92-7.89 (m, 3H), 7.80-7.76 (m, 1 H), 7.64 (s, 1 H), 7.45-7.41 (m, 2H), 7.36-7.30 (m, 1 H), 4.83-4.76 (m, 1 H), 2.65 (s, 6H), 2.61 -2.55 (m, 2H), 2.21 -2.16 (m, 2H), 2.10 (s, 3H) ppm. LCMS (ESI) m/z: [M+H]+=519.2.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 78

34
[ 685824-73-1 ]
[ 7326-73-0 ]
(S)-3-(N,N-dimethylsulfamoyl)-N-(1-oxo-1-((4-phenylthiazol-2-yl)amino)propan-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 25℃; for 2h;	To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (92.70 mg, 404.34 pmol) in DCM (3 ml_) was added HATU (169.12 mg, 444.78 pmol) and DIPEA (156.77 mg, 1 .21 mmol, 21 1 .29 pL), then intermediate i-4b (100 mg, 404.34 pmol) was added to the mixture. The mixture was stirred at 25 C for 2 hr. The reaction mixture was concentrated under reduced pressure to give a solid. To the solid was added MeOH (80 ml_) and stirred for 10 min and then filtered, the solid was collected by filtration and dried in vacuum to give compound 12 as a white solid. 1 HNMR (400 MHz, DMSO-d6) d 12.48 ( s,1 H) , 9.13 (d, J=6.4 Hz, 1 H), 8.30-8.23 (m, 2H), 7.92-7.89 (m, 3H), 7.80-7.76 (m, 1 H), 7.64 (s, 1 H), 7.46-7.41 (m, 2H), 7.36-7.29 (m, 1 H), 4.76-4.69 (m, 1 H), 2.65 (s, 6H), 1 .49 (d, J= 7.2 Hz, 3H) ppm. LCMS (ESI) m/z: [M+H]+=459.0. SFC HPLC: OD-3-EtOH(DEA)-5-40-3mL-35T.lc, 2.455 min.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 81

35
[ 7326-73-0 ]
2-amino-N-(3-phenylphenyl)acetamide trifluoroacetate [ No CAS ]
3-(dimethylsulfamoyl)-N-[2-oxo-2-(3-phenylanilino)ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (45.59 mg, 198.87 pmol) in DCM (3 mL) was added DIPEA (77.1 1 mg, 596.62 pmol) and HATU (1 13.43 mg, 298.31 pmol). The mixture was stirred at 25 C for 10 min and then intermediate i-5b was added and the mixture was stirred at 25 C for 2hr. The reaction mixture was concentrated in vacuo to give a residue. To the residue was added a mixture of methanol:water=1 :1 , v/v, (4 mL) and stirred for 10 min, then filtered, the filter cake was washed with methanol (2 mL) and then lyophilized to give compound 40 as a white solid. 1 H NMR (400 MHz, DMSO-d6) d 10.22 (s, 1 H), 9.24 (m, 1 H), 8.19-8.32 (m, 2H), 7.90-8.00 (m, 2H), 7.73- 7.86 (m, 1 H), 7.56-7.65 (m, 3H), 7.32-7.51 (m, 5H) , 4.14 (m, 2H), 2.63-2.68 (m, 6H) ppm ; LCMS (ESI) m/z: [M+H]+=438.2.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 83

36
[ 7326-73-0 ]
2-amino-N-[4-(2-pyridyl)thiazol-2-yl]acetamide trifluoroacetate [ No CAS ]
3-(dimethylsulfamoyl)-N-[2-oxo-2-[[4-(2-pyridyl)thiazol-2-yl]amino]ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (98.73 mg, 430.66 pmol) in DCM (2 ml_) was added HATU (180.13 mg, 473.73 pmol) and DIPEA (278.30 mg, 2.15 mmol) at 25 C. The mixture was stirred at 25 C for 10 min, then intermediate 9a (150 mg, 430.66 pmol) was added and stirred for 1 h. The reaction mixture was evaporated to dryness. To the residue was added MeOH (30 ml_) and stirred for 10 min, then filtered and the filter cake was washed with MeOH (30 ml_). The filter cake was evaporated to dryness to give compound 32 as an off-white solid. 1 HNMR (400MHz, DMSO-de) d = 12.49 (br s, 1 H), 9.30-9.28 (m, 1 H), 8.60 (d, J= 4.0 Hz, 1 H), 8.27-8.21 (m, 2H), 7.98-7.92 (m, 2H), 7.92-7.86 (m, 1 H), 7.85-7.80 (m, 2H), 7.36-7.32 (m, 1 H), 4.24 (d, J= 5.6 Hz, 2H), 2.66 (s, 6H) ppm ; LCMS (ESI) m/z: [M+H]+=446.2.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 86

37
[ 7326-73-0 ]
(2S)-2-amino-N-(4-phenylthiazol-2-yl)pentanamide trifluoroacetate [ No CAS ]
3-(dimethylsulfamoyl)-N-[(1S)-1-[(4-phenylthiazol-2-yl)carbamoyl]butyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of HATU (36.25 mg, 95.35 pmol) and <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (20.04 mg, 87.40 pmol) in DCM (2.0 mL) was added DIPEA (41 .07 mg, 317.82 pmol) in one portion at 20 C under N2. The mixture was stirred at 20 C for 10 min. Then (2S)-2-amino-N-(4-phenylthiazol-2-yl)pentanamide (50.0 mg, 128.41 pmol, TFA salt) was added and the mixture was stirred at 20 C for 2 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (TFA condition; column: Boston pH-lex 150*25 10 pm; mobile phase: [water (0.1 %TFA)- ACN]; B%: 57%-76%, 8 min) and lyophilized to give compound 17 as a white solid. 1 H NMR (400MHz, DMSO-de) d 12.52 (s, 1 H), 9.05 (d, J = 7.6 Hz, 1 H), 8.29-8.27 (m, 2H), 7.93-7.90 (m, 3H), 7.81 -7.79 (m, 1 H), 7.64 (s, 1 H), 7.54-7.39 (m, 2H), 7.38-7.27 (m, 1 H), 4.76-4.70 (m, 1 H), 2.68-2.65 (m, 6H), 1 .86-1 .83 (m, 2H), 1 .58-1 .31 (m, 2H), 0.96-0.92 (m, 3H) ppm. LCMS (ESI) m/z: [M+H]+ = 487.1. Chiral HPLC: Amycoat-MeOH(DEA)-40-7min-3mL, 2.022 min.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 106-107

38
[ 7326-73-0 ]
2-amino-N-(4-(o-tolyl)thiazol-2-yl)acetamide [ No CAS ]
3-(dimethylsulfamoyl)-N-[2-[[4-(o-tolyl)thiazol-2-yl]amino]-2-oxoethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (1 1 1 .24 mg, 485.21 pmol) in DCM (2.0 ml_) was added HATU (202.94 mg, 533.73 pmol) and DIEA (188.13 mg, 1 .46 mmol). The mixture was stirred at 20 C for 0.5 hr. Intermediate D (120.0 mg, 485.21 pmol) was added and the mixture was stirred at 20 C for 1 .5 hr. The reaction mixture was poured into water (10.0 ml_) and extracted with EtOAc (10.0 ml_*3). The combined organic extract were washed with brine (10.0 ml_), dried over Na2S04, filtered and concentrated. The crude product was triturated with MeOH (10.0 ml_). The solid was collected by filtration and dried in vacuo to give compound 16 as white solid. 1 H NMR (400 MHz, DMSO-de) d 12.40 (s, 1 H), 9.31 -9.28 (m, 1 H), 8.26-8.22 (m, 2H), 7.95-7.93 (m, 1 H), 7.82-7.80 (m, 1 H), 7.59-7.57 (m, 1 H), 7.27-7.25 (m, 4H), 4.22 (d, J = 5.6 Hz, 2H), 2.65 (s, 6H), 2.43 (s, 3H) ppm LCMS (ESI) m/z: [M+H]+ =459.0

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 100

39
[ 7326-73-0 ]
2-amino-N-(4-(m-tolyl)thiazol-2-yl)acetamide [ No CAS ]
3-(dimethylsulfamoyl)-N-[2-[[4-(m-tolyl)thiazol-2-yl]amino]-2-oxoethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (46.35 mg, 202.17 pmol) in DCM (1 .0 mL) were added HATU (84.56 mg, 222.39 pmol) and DIEA (78.39 mg, 606.51 pmol) at 20C. The mixture was stirred at 20C for 0.5 hr. Then intermediate i-18c (50.0 mg, 202.17 pmol) was added and the mixture was stirred at 20C for 1 .5 hr. The reaction mixture was poured into water (5.0 mL) and extracted with EtOAc (10.0 ml_3). The combined organic extracts were washed with brine (10.0 ml_), dried over Na2S04, filtered and concentrated. The residue was purified by prep-HPLC (column: Phenomenex Synergi C1 8 15025*10 pm; mobile phase: [water (0.1 %TFA)-ACN]; B%: 42%-72%, 9 min) and lyophilized to give compound 1 as white solid. 1 H NMR (400 MHz, DMSO-de) d = 12.45 (s, 1 H), 9.30-9.27 (m,1 H), 8.26-8.22 (m, 2H), 7.94 (d, J=7.6 Hz, 1 H), 7.82-7.77 (m, 1 H), 7.73-7.65 (m, 2H), 7.60 (s, 1 H), 7.32-7.30 (m, 1 H), 7.14 (d, J=7.6 Hz, 1 H), 4.23 (d, J=5.6 Hz, 2H), 2.65 (s, 6H), 2.35 (s, 3H) ppm LCMS (ESI) m/z: [M+H]+ = 459.0

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 101-102

40
[ 142349-29-9 ]
[ 7326-73-0 ]
3-(dimethylsulfamoyl)-N-[2-oxo-2-[[4-(p-tolyl)thiazol-2-yl]amino]ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (139 mg, 606.32 pmol) in DCM (2.0 mL) were added DIEA (235.09 mg, 1 .82 mmol) and HATU (253.59 mg, 666.95 pmol), the mixture was stirred at 20 C for 0.5 hr. Then intermediate D (1 50.00 mg, 606.51 pmol) was added at 20 C and the mixture was stirred at 20 C for 1 .5 hr. The reaction mixture was poured into water (10.0 mL) and extracted with EtOAc (10.0 mL*3). The combined organic extracts were washed with brine (10.0 mL), dried over Na2S04, filtered and concentrated. The crude product was triturated with MTBE (10.0 mL). The solid was collected by filtration and dried in vacuo to give compound 31 as a white solid. 1 H NMR (400 MHz, DMSO-de) d = 12.45 (s, 1 H), 9.30-9.27 (m, 1 H), 8.26-8.22 (m, 2H), 7.94 (d, J=8.0 Hz, 1 H), 7.82-7.77 (m, 3H), 7.56 (s,1 H), 7.24 (d, J=8.0 Hz, 2H), 4.23 (d, J=5.6 Hz, 2H), 2.65 (s, 6H), 2.32 (s, 3H) ppm LCMS (ESI) m/z: [M+H]+ =459.0

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 103

41
[ 7326-73-0 ]
2-amino-N-(4-phenylthiazol-2-yl)acetamide hydrochloride [ No CAS ]
3-(dimethylsulfamoyl)-N-[2-oxo-2-[(4-phenylthiazol-2-yl)amino]ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[7326-73-0]3-(dimethylsulfamoyl)benzoic acid</strong> (75.72 mg, 330.31 pmol) in DCM (10 ml_) was added HATU (125.59 mg, 330.31 pmol) and DIPEA (155.24 mg, 1 .20 mmol). The solution was stirred for 10 min and then intermediate i-1 b (81 mg, 300.28 pmol) was added. The solution was stirred at 30 C for 12hr. The reaction solution was poured into water (50 ml_) and extracted with EtOAc (100 ml_). The organic layer was washed with brine (50 ml_), dried (Na2SC>4) and concentrated in vacuum. To the residue was added MeOH (20 ml_) and stirred for 20 min, a white solid was formed. The solid was filtered and dried in vacuum to give compound 13 as a white solid. LCMS (ESI) m/z: [M+H]+ = 444.9. 1 H NMR (400 MHz, DMSO-d6) d= 12.49 (s, 1 H), 9.32 (t, J=5.6 Hz, 1 H), 8.27-8.25 (m, 2H), 7.96-7.90 (m, 3H), 7.81 -7.80 (m, 1 H), 7.64 (s, 1 H), 7.46-7.42 (m, 2H), 7.33-7.30 (m, 1 H), 4.23 (d, J=5.6 Hz, 2H), 2.65 (s, 6H) ppm.

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 76

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Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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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
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
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
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
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. 7326-73-0 ] {[proInfo.proName]}

Quality Control of [ 7326-73-0 ]

Related Doc. of [ 7326-73-0 ]

Product Details of [ 7326-73-0 ]

Calculated chemistry of [ 7326-73-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7326-73-0 ]

Application In Synthesis of [ 7326-73-0 ]

[ 7326-73-0 ] Synthesis Path-Upstream 1~1

[ 7326-73-0 ] Synthesis Path-Downstream 1~41

Related Functional Groups of [ 7326-73-0 ]

Aryls

Amines

Carboxylic Acids

Sulfamides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 7326-73-0 ]