Trifluoroacetic acid → HCID 53258567, compound

HRID 2039739Notes

Reaction equation

HRID 2039739 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[C:16]3[C:23]([C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[C:16]3[C:23]([C:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:31])=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58327713HCID 58327713, compound

Product 1

HCID 53258567HCID 53258567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of tert-butyl(3-((5-benzoyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)phenyl)carbamate (5.8 g, 13.5 mmol) in DCM (50 mL) was added 25 mL of TFA. The mixture was heated at 50° C. for 1 hour. Solvent was removed under reduced pressure. The residue was washed with DCM and dried on high vacuum to give an off-white solid. M.p.=280-282° C.; 400 MHz 1HNMR (DMSO-d6) δ 13.11 (s, 1H), 11.56 (s, 1H), 8.51 (s, 1H), 8.09 (s, 1H), 8.01 (s, 1H), 7.86 (d, J=7.6 Hz, 2H), 7.70 (t, J=10 Hz, 2H), 7.60 (t, J=7.2 Hz, 2H), 7.46 (t, J=8.0 Hz, 1H), 6.95 (d, J=7.2 Hz, 1H); LCMS [M+H] 330.

Workup

  1. customSolvent was removed under reduced pressure
  2. washThe residue was washed with DCM
  3. customdried on high vacuum
  4. customto give an off-white solid

Sources & evidence

ORD record
ord-43953366c1d14835956307440eaec5d8
Source dataset
uspto-grants-2013_11
Patent number
US08580803B2

Reaction notes

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