Potassium Carbonate → N-((1SR,4SR,7RS)-2-benzyl-2-azabicyclo[2.2.1]heptan-7-yl)-1H-indazol-5-amine

HRID 75689Notes

Reaction equation

HRID 75689 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:14]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21](C(=O)C(C)(C)C)[N:20]=[CH:19]4)[CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12C(NC3C=C4C(=CC=3)N(C(=O)C(C)(C)C)N=C4)C(CC1)CN2.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:14]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[CH:19]4)[CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58306368HCID 58306368, compoundHCID 67234529HCID 67234529, compound

Product 1

HCID 53246934N-((1SR,4SR,7RS)-2-benzyl-2-azabicyclo[2.2.1]heptan-7-yl)-1H-indazol-5-amineYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(5-((1SR,4SR,7RS)-2-benzyl-2-azabicyclo[2.2.1]heptan-7-ylamino)-1H-indazol-1-yl)-2,2-dimethylpropan-1-one (the intermediate benzyl compound of Example 11, 175 mg, 0.44 mmol) in methanol (2.5 mL) was treated with potassium carbonate (72 mg, 0.52 mmol), and the mixture was stirred for 18 h. The mixture was partitioned between ethyl acetate and water, and the organic phase was dried over sodium sulfate and evaporated to a residue. Chromatography of the residue on silica gel afforded the title compound (70 mg, 50%). 1H NMR (CDCl3) δ 9.80 (br s, 1H), 7.88 (s, 1H), 7.39-7.21 (m, 6H), 6.92-6.85 (m, 2H), 3.80 (m, 1H), 3.63 (s, 1H), 3.16-3.12 (m, 2H), 2.40-2.37 (m, 1H), 2.04-1.96 (m, 2H), 1.85-1.76 (m, 2H), 1.60-1.40 (m, 2H)

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customevaporated to a residue

Sources & evidence

ORD record
ord-26aac5d1bcf0442bbeca6bf7447b2d2e
Source dataset
uspto-grants-2014_09
Patent number
US08835457B2

Reaction notes

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