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

HRID 1484922Notes

Reaction equation

HRID 1484922 reaction equation
[Br:1][C:2]1[C:3]([NH:22][C:23]2[CH:27]=[C:26]([CH:28]3[CH2:30][CH2:29]3)[NH:25][N:24]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH3:31][C:32](OC(C)=O)=[O:33]>C1COCC1.O>[C:32]([N:25]1[C:26]([CH:28]2[CH2:29][CH2:30]2)=[CH:27][C:23]([NH:22][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([C:8]3[S:12][C:11]([S:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])(=[O:14])=[O:15])=[CH:10][CH:9]=3)[N:4]=2)=[N:24]1)(=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 581695025-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide

Product 1

HCID 581695145-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

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

Procedure

To the mixture of 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide (200 mg, 0.39 mmol) in THF/H2O (2 mL/2 mL), Ac2O (0.2 mL, 1.95 mmol, 5.0 eq) was added dropwise. The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was filtered, and the solid was concentrated with ethanol to bring residual water off to afford crude 5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide (used for the next step without further purification). LC-MS (m/z)=556.0, 558.0 [M+H]+

Workup

  1. additionwas added dropwise
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe solid was concentrated with ethanol

Sources & evidence

ORD record
ord-c40fc6ed2d054e668e75dc9cdd03b479
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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