Acetic Anhydride → HCID 58169517, compound

HRID 1484928Notes

Reaction equation

HRID 1484928 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[S:11][C:12]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH:27]4[CH2:29][CH2:28]4)[NH:24][N:23]=3)[C:18]([Br:30])=[CH:17][N:16]=2)=[CH:13][CH:14]=1)=[O:9])(=[O:3])[CH3:2].[C:31](OC(=O)C)(=[O:33])[CH3:32]>C1COCC1.O>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[S:11][C:12]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH:27]4[CH2:29][CH2:28]4)[N:24]([C:31](=[O:33])[CH3:32])[N:23]=3)[C:18]([Br:30])=[CH:17][N:16]=2)=[CH:13][CH:14]=1)=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58169404HCID 58169404, compound

Product 1

HCID 58169517HCID 58169517, compoundYield 98.6%

Reagents, catalysts & solvents 1

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

Procedure

To N-(2-acetamidoethyl)-5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carboxamide (273.8 mg, 0.56 mmol, 1.0 equiv.), acetic anhydride (114.2 mg, 1.1 mmol, 2.0 equiv.) in THF/H2O (10 ml/1 mL) was stirred at 23° C. for 2 hour. Then the mixture was extracted with THF (6×40 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated give N-(2-acetamidoethyl)-5-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-bromopyrimidin-2-yl)thiophene-2-carboxamide (294.0 mg, 98.5%) as pale yellow solid. LC-MS (m/z)=533.1 [M+H]+;

Workup

  1. extractionThen the mixture was extracted with THF (6×40 ml)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e1dadf6e16a4f4f98b43ff9557c70dc
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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