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Acetyl chloride → N-(3-[2-(2-sulfamoylpropan-2-yl)-1,3-thiazol-5-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide

HRID 410595
Notes
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Reaction equation

HRID 410595 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]([S:27]([NH2:30])(=[O:29])=[O:28])([CH3:26])[CH3:25])=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C(Cl)Cl.CO>[S:27]([C:24]([C:22]1[S:23][C:19]([C:4]2[CH:3]=[C:2]([NH:1][C:38](=[O:40])[CH3:39])[CH:7]=[C:6]([NH:8][C:9]3[N:14]=[C:13]([C:15]([F:16])([F:18])[F:17])[CH:12]=[CH:11][N:10]=3)[CH:5]=2)=[CH:20][N:21]=1)([CH3:26])[CH3:25])(=[O:29])(=[O:28])[NH2:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 584561682-[5-(3-Amino-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propane-2-sulfonamide

Product 1

HCID 58456282N-(3-[2-(2-sulfamoylpropan-2-yl)-1,3-thiazol-5-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamideYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344DichloromethaneSolvent

Procedure

2-[5-(3-Amino-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propane-2-sulfonamide (Example 71, 90 mg, 0.196 mmol) was suspended in CH2Cl2 (5 mL) with triethylamine (55 μL, 0.393 mmol), and acetyl chloride (28 μL, 0.393 mmol) was added. After stirring for 1 h at room temperature, additional acetyl chloride (28 μL, 0.393 mmol) and triethylamine (55 μL, 0.393 mmol) were added. After another 1 h at room temperature, the suspension was diluted with MeOH, silica was added, and the mixture was evaporated to dryness. Flash chromatography (dry load, 40-100% ethyl acetate in hexanes) afforded N-(3-[2-(2-sulfamoylpropan-2-yl)-1,3-thiazol-5-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}-phenyl)acetamide (34 mg, 35%) as a white solid. MS ESI: [M+H]+ m/z 501.0. 1H NMR (500 MHz, DMSO-d6) δ 10.35 (s, 1H), 10.07 (s, 1H), 8.82 (d, J=4.9, 1H), 7.94 (s, 1H), 7.91 (s, 1H), 7.83 (s, 1H), 7.61 (s, 1H), 7.29 (d, J=4.9, 1H), 7.05 (s, 2H), 2.05 (s, 3H), 1.79 (s, 6H). rhSYK activity=+++

Workup

  1. additionwas added
  2. waitAfter another 1 h at room temperature
  3. additionwas added
  4. customthe mixture was evaporated to dryness
  5. dry with materialFlash chromatography (dry load, 40-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9b78274353b04d8d8096e6cdc6fd0513
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759366B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes