Methanol → HCID 24997112, compound

HRID 1967114Notes

Reaction equation

HRID 1967114 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C@@H:13]([NH:25][C:26]([C:28]1[CH:32]=[C:31]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=2)[O:30][CH:29]=1)=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22].CO.NN>C1COCC1>[NH2:3][CH2:12][C@@H:13]([NH:25][C:26]([C:28]1[CH:32]=[C:31]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=2)[O:30][CH:29]=1)=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 67065454HCID 67065454, compound

Product 1

HCID 24997112HCID 24997112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-furancarboxamide (200 mg, 0.38 mmol) was dissolved in THF (10 mL) and MeOH (10 mL) at RT and treated with hydrazine (0.19 mL, 3.8 mmole). After 24 h, the solution was concentrated and purified on silica using 8% MeOH in DCM (1% NH4OH) to give the title compound as a white solid. The free base was dissolved in DCM (5 mL) and treated with 4M HCl in dioxane (4 mL). After 5 min, the reaction solution was concentrated under vacuum to give the title compound (55 mg) as a di-HCl salt: LC-MS (ES) m/z=393 (M+H)+, 1H NMR (d6-DMSO) δ 8.78 (d, J=8.9 Hz, 1H), 8.38 (s, 1H), 8.16 (bs, 2H), 7.69 (d, J=7.6 Hz, 1H), 7.59 (m, 2H), 7.49 (s, 1H), 7.44 (m, 1H), 7.35 (s, 1H), 6.58 (s, 1H), 4.52 (m, 1H), 3.99 (s, 3H), 3.22 (m, 2H) and 3.07 (m, 2H).

Workup

  1. concentrationthe solution was concentrated
  2. custompurified on silica using 8% MeOH in DCM (1% NH4OH)

Sources & evidence

ORD record
ord-9ae30d458d5744ae9c9dd3e40d7ae85c
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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