Acetyl chloride → HCID 67391725, compound

HRID 406101Notes

Reaction equation

HRID 406101 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[NH2:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[NH:26][C:27]2[C:28]3[C:35]([CH3:36])=[C:34]([C:37]([NH2:39])=[O:38])[S:33][C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:14]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([NH:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[NH:26][C:27]2[C:28]3[C:35]([CH3:36])=[C:34]([C:37]([NH2:39])=[O:38])[S:33][C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:14]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67391053HCID 67391053, compound

Product 1

HCID 67391725HCID 67391725, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (21 μl) was added at 0° C. to a mixture of 4-[2-((1S,3S)-3-amino-cyclopentyloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide trifluoroacetate (cpd. 229, 206 mg) and DIPEA (348 μl) in DCM (25 ml) and stirred at rt for 4 hours. The reaction mixture was concentrated, diluted with water and extracted with DCM. The organic layer was dried, concentrated and the crude was purified by chromatography to give the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-d51dfb89b9df4306b2381020711200fd
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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