Trifluoroacetic acid → HCID 58327699, compound

HRID 2039740Notes

Reaction equation

HRID 2039740 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[C:24]([C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:23][NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:17]3[C:24]([C:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:32])=[CH:23][NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58327749HCID 58327749, compound

Product 1

HCID 58327699HCID 58327699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of tert-butyl(4-((5-benzoyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)benzyl)carbamate (0.18 g, 0.41 mmol) in DCM (1.5 mL) was added 0.5 mL of TFA. The mixture was heated at 50° C. for 1 hour. The solvent was removed under reduced pressure. The residue was washed with DCM and dried on high vacuum give a yellow solid. M.p.=255-257° C.; 400 MHz 1HNMR (DMSO-d6) δ 13.05 (s, 1H), 11.43 (s, 1H), 8.48 (s, 1H), 7.98-7.96 (m, 3H), 7.85 (d, J=8.4 Hz, 2H), 7.70 (t, J=7.6 Hz, 1H), 7.60 (t, J=7.6 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 4.03 (q, J=5.2 Hz, 2H); LCMS [M+H] 344.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThe residue was washed with DCM
  3. customdried on high vacuum
  4. customgive a yellow solid

Sources & evidence

ORD record
ord-5b31f839dc4142b281fab0f792049f94
Source dataset
uspto-grants-2013_11
Patent number
US08580803B2

Reaction notes

Loading…