Methanol → HCID 11244984, compound

HRID 912637Notes

Reaction equation

HRID 912637 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3C(OC)=O)=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO>O1CCCC1.O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][NH:22]3)=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11177232HCID 11177232, compound

Product 1

HCID 11244984HCID 11244984, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-({[(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)amino]carbonyl}amino)-1H-indazole-1-carboxylate (5.67 g, 14 mmol) in tetrahydrofuran (20 ml) was treated with A 5M solution of sodium hydroxide in methanol (8 ml, 40 mmol). After stirring for 30 minutes, the reaction mixture was diluted with water and filtered. The solid was air-dried and then treated with ethanolic HCl to provide the title compound as the hydrochloride salt. 1H NMR (DMSO-d6) δ 1.06 (t, 1.8H, EtOH), 1.27 (s, 9H), 1.75-1.88 (m, 1H), 2.40-2.48 (m, 1H), 2.76-2.88 (m, 1H), 2.90-3.01 (m, 1H), 3.44 (q, 1.2H, EtOH), 5.12 (m, 1H), 6.84 (br d, 1H), 7.05 (d, 1H), 7.20, (m, 1H), 7.26 (s, 2H), 7.31 (s, 1H), 7.69 (d, 1H), 8.10 (s, 1H), 8.70 (s, 1H); MS (ESI+): 349 (M+H)+; Elemental: Calculated for C21H24N4O.HCl.0.6EtOH.0.6H2O: C, 62.98; H, 7.09; N, 13.23; Found: C, 63.09; H, 6.97; N, 13.18.

Workup

  1. filtrationfiltered
  2. customThe solid was air-dried
  3. additiontreated with ethanolic HCl

Sources & evidence

ORD record
ord-393b013b912644129408faf8f093cc0c
Source dataset
uspto-grants-2011_09
Patent number
US08026256B2

Reaction notes

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