Trifluoroacetic acid → N-tert-butyl-2-(6-fluoro-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246758Notes

Reaction equation

HRID 246758 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[N:19]([CH2:27][CH2:28][CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[N:19]([CH2:27][CH2:28][CH2:29][S:30]([CH3:33])(=[O:31])=[O:32])[N:18]=3)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71280274N-tert-butyl-2-(6-fluoro-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71279423N-tert-butyl-2-(6-fluoro-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-tert-butyl-2-(6-fluoro-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (55 mg, 0.077 mmol) in dichloromethane (2 mL) was added drop-wise trifluoroacetic acid (2 mL) at room temperature and the reaction mixture was stirred for 2 hours. The solvent was removed under reduced pressure. The residue was triturated with MeOH then decanted and dried and dried to give N-tert-butyl-2-(6-fluoro-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (26 mg, 72%) as a white solid. LCMS: (M+H)+=473; (M+Na)+=495; 1H NMR (300 MHz, DMSO): δ 12.84 (s, 1H), 9.09 (s, 1H), 8.51-8.46 (m, 1H), 8.38 (s, 1H), 7.93 (s, 1H), 7.74 (d, 1H, J=9.9 Hz), 7.18 (t, 1H, J=9.0 Hz), 4.63 (t, 2H, J=6.6 Hz), 3.22 (t, 2H, J=7.8 Hz), 2.99 (s, 3H), 2.33 (t, 2H, J=7.4 Hz), 1.52 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with MeOH
  3. customthen decanted
  4. customdried
  5. customdried

Sources & evidence

ORD record
ord-7602e435649048fabafd4af27dda223f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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