Acetic Anhydride → HCID 9984757, compound

HRID 491480Notes

Reaction equation

HRID 491480 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[CH:8]1([CH2:14][CH2:15][N:16]2[C:20]3[N:21]=[C:22]([C:25]#[N:26])[N:23]=[CH:24][C:19]=3[CH:18]=[C:17]2[CH2:27][N:28]2[C:32](=[O:33])[C:31]3([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:30]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:29]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(OC(=O)C)(=O)C>ClCCl.C(N(CC)CC)C>[C:3]([N:36]1[CH2:37][CH2:38][C:31]2([N:30]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:29][N:28]([CH2:27][C:17]3[N:16]([CH2:15][CH2:14][CH:8]4[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[C:20]4[N:21]=[C:22]([C:25]#[N:26])[N:23]=[CH:24][C:19]=4[CH:18]=3)[C:32]2=[O:33])[CH2:34][CH2:35]1)(=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68981335HCID 68981335, compound

Product 1

HCID 9984757HCID 9984757, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 7-(2-cyclohexyl-ethyl)-6-(4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile trifluoroacetic acid salt (142 mg, 0.28 mol) in dichloromethane (2 ml), triethylamine (395 μl) and acetic anhydride (54 μl, 0.57 mmol) are added at 0° C. The reaction mixture is stirred for over night at room temperature, quenched with ice-water and extracted with ethyl acetate. The combined extracts are washed with H2O, brine and dried over sodium sulphate. Chromatography on silica gel gives 90 mg of 6-(8-acetyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7-(2-cyclohexyl-ethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 58% yield.

Workup

  1. customquenched with ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-9a8b9552e33a4d3faac084728bd36577
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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