Acetic Anhydride → 5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)-N-tert butylthiophene-2-sulfonamide

HRID 1484935

Reaction equation

HRID 1484935 reaction equation
[Br:1][C:2]1[C:3]([NH:21][C:22]2[CH:26]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[NH:24][N:23]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH3:30][C:31](OC(C)=O)=[O:32]>C1COCC1.O>[C:31]([N:24]1[C:25]([CH:27]2[CH2:28][CH2:29]2)=[CH:26][C:22]([NH:21][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([C:8]3[S:12][C:11]([S:13]([NH:16][C:17]([CH3:19])([CH3:20])[CH3:18])(=[O:14])=[O:15])=[CH:10][CH:9]=3)[N:4]=2)=[N:23]1)(=[O:32])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 581693555-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 581695675-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)-N-tert butylthiophene-2-sulfonamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide (1.6 g, 3.21 mmol, 1.0 eq) in THF/H2O (30 mL/15 mL), Ac2O (0.64 g, 6.42 mmol, 2.0 eq) was added dropwise. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was filtered to afford compound 5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)-N-tert butylthiophene-2-sulfonamide (1.6 g, 92%). LC-MS (m/z)=539 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-8f9f625f22874502bf2efd72fe0a3af9
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Linked notes

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