Trifluoroacetic acid → HCID 58421738, compound

HRID 406061Notes

Reaction equation

HRID 406061 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[O:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[C:23]2[C:30]([CH3:31])=[C:29]([C:32](=[O:34])[NH2:33])[S:28][C:24]=2[N:25]=[CH:26][N:27]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[O:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[C:23]2[C:30]([CH3:31])=[C:29]([C:32]([NH2:33])=[O:34])[S:28][C:24]=2[N:25]=[CH:26][N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 76781870HCID 76781870, compound

Product 1

HCID 58421738HCID 58421738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of 2.1 g 1S,2S) {2-(2-(6-carbamoyl-5-methyl-thieno[2,3-d]pyrimidin-4-ylamino)-5-fluoro-phenoxy]-cyclopentyl}-carbamic acid tert-butyl ester, and 1.24 ml trifluoroacetic acid in 50 ml DCM was stirred for 3 days at 46° C. The mixture was concentrated, diluted with toluenel and concentrated. The residue was extracted with DCM and water, whereby the water layer had the pH range of 10. The organic layer was dried and concentrated in vacuo. The residue was purified by chromatography.

Workup

  1. additionA reaction mixture of 2.1 g
  2. concentrationThe mixture was concentrated
  3. additiondiluted with toluenel
  4. concentrationconcentrated
  5. extractionThe residue was extracted with DCM and water, whereby the water layer
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-65925539c7ca4850b75fa8729fee029e
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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