Trifluoroacetic acid → HCID 90312907, compound

HRID 1523877Notes

Reaction equation

HRID 1523877 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([NH:30][C@H:31]([C:33]([O:35]C(C)(C)C)=[O:34])[CH3:32])(=[O:29])=[O:28])=[CH:17][C:16]=2[F:40])=[CH:11][N:10]=1>C(Cl)Cl>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([NH:30][C@H:31]([C:33]([OH:35])=[O:34])[CH3:32])(=[O:29])=[O:28])=[CH:17][C:16]=2[F:40])=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90313737HCID 90313737, compound

Product 1

HCID 90312907HCID 90312907, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of tert-butyl N-{[4′-(2-aminopyrimidin-5-yl)-3′-fluorobiphenyl-2-yl]sulfonyl}-L-alaninate (80 mg, 0.17 mmol) in DCM (1 mL) at rt. After 2 hours, the solution was concentrated to dryness and purified by HPLC to afford the title compound (70 mg, 89%). MS (ESI): mass calcd. for C19H17FN4O4S, 416.10; m/z found, 417.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.72 (s, 2H), 8.10 (dd, J=8.0, 1.2, 1H), 7.66 (m, 1H), 7.61-7.53 (m, 2H), 7.37 (m, 3H), 3.73 (q, J=7.2, 1H), 1.31 (d, J=7.2, 3H).

Workup

  1. concentrationthe solution was concentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-f1789ab1d8554bf9b2e9a778689a1544
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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