Trifluoroacetic acid → HCID 57619315, compound

HRID 1256842Notes

Reaction equation

HRID 1256842 reaction equation
[C:1]([O:5][C:6](=[O:43])[N:7]([C:16]1[S:17][C:18]([CH:21]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([Cl:32])[CH:30]=3)[N:25]([Si](C(C)C)(C(C)C)C(C)C)[CH:24]=2)O)=[CH:19][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[C:1]([O:5][C:6](=[O:43])[N:7]([C:16]1[S:17][C:18]([CH2:21][C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([Cl:32])[CH:30]=3)[NH:25][CH:24]=2)=[CH:19][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57619456HCID 57619456, compound

Product 1

HCID 57619315HCID 57619315, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of {5-[(5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-thiazol-2-yl}-(4-fluoro-benzyl)-carbamic acid tert-butyl ester (627, 120 mg, 0.186 mmol) in acetonitrile (3 mL) was added trifluoroacetic acid (0.14 mL, 1.86 mmol) and triethylsilane (0.30 mL, 1.86 mmol). The resulting mixture was stirred for 2 hours at 40° C. The solvent was then removed in vacuo and the residue was used directly in the next step.

Workup

  1. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-fdd7006eecea476aa0c3973196874e76
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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