Trifluoroacetic acid → HCID 178492379, compound

HRID 900100Notes

Reaction equation

HRID 900100 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:27]3[N:23]([C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:25][N:26]=3)[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[N:20]([CH2:38][C:39](=[O:52])[N:40]([CH:49]([CH3:51])[CH3:50])[C:41]3[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=3)[C:19]2=[O:53])=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:27]3[N:23]([C:24]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[N:25][N:26]=3)[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[N:20]([CH2:38][C:39]([N:40]([CH:49]([CH3:50])[CH3:51])[C:41]3[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=3)=[O:52])[C:19]2=[O:53])=[N:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 693136083-(6-{[isopropyl-(6-methoxy-pyridin-3-yl)-carbamoyl]-methyl}-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl)-indazole-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 178492379HCID 178492379, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step A, 3-(6-{[isopropyl-(6-methoxy-pyridin-3-yl)-carbamoyl]-methyl}-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl)-indazole-1-carboxylic acid tert-butyl ester, was dissolved in CH2Cl2 (8 mL) and TFA (2 mL) was added. The reaction was stirred at room temperature for 24 hours and was concentrated in vacuo. Purification by medium pressure chromatography eluting with a solvent gradient (1% MeOH in EtOAc to 5% MeOH in EtOAc) provided 172 mg of 2-[4-(1H-indazol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. 1H NMR (CD3OD) δ 8.04 (d, 1H), 7.88 (d, 1H), 7.64 (m, 2H), 7.56 (d, 2H), 7.49 (t, 2H), 7.39 (q, 3H), 7.31 (t, 1H), 7.19 (t, 1H), 7.11 (t, 1H), 6.95 (d, 1H), 6.86 (m, 1H), 4.72 (m, 1H), 4.59 (m, 1H), 4.41 (t, 1H), 3.99-4.12 (m, 2H), 3.90 (m, 4H), 0.95 (m, 6H); MS 613.8 (M+1), 611.5 (m−1).

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification by medium pressure chromatography
  3. washeluting with a solvent gradient (1% MeOH in EtOAc to 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-58fe0cf462ed4c08a04931bbf858162d
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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