Methylamine → HCID 18447414, compound

HRID 1269758Notes

Reaction equation

HRID 1269758 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)=[O:10])[CH2:4][CH2:3]1.CN.[B-][C:23]#[N:24].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:23][NH:24][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)=[O:10])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 20587905Sodium cyanoborohydride [MI]HCID 22934099HCID 22934099, compound

Product 1

HCID 18447414HCID 18447414, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Acetic acid (0.096 ml) was added to a solution of the N-(4-oxocyclohexyl)-1H-indazole-5-carboxamide (40.0 mg, 0.155 mmol) obtained in Example 160 in methanol (1.2 ml), and the resulting solution was maintained at room temperature for 30 minutes. To this solution was added a 40% aqueous methylamine solution (60.0 mg, 0.777 mmol), and the resulting mixture was maintained at room temperature for another 2 hours. Then, a solution of sodium cyanotrihydroborate (48.7 mg, 0.777 mmol) in methanol (0.6 ml) was added dropwise thereto, and the resulting mixture was stirred for 22 hours while being maintained at room temperature. A 1N aqueous sodium hydroxide solution (0.8 ml) was added to the reaction solution, and the resulting mixture was stirred while being maintained at room temperature, and was then concentrated to dryness. The resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=10/1/0.1) to obtain N-[4-(methylamino)cyclohexyl]-1H-indazole-5-carboxamide (an isomer having a lower polarity) (12.2 mg, 29%) and N-[4-(methylamino)cyclohexyl]-1H-indazole-5-carboxamide (an isomer having a higher polarity) (28.3 mg, 67%).

Workup

  1. temperaturethe resulting mixture was maintained at room temperature for another 2 hours
  2. temperaturewhile being maintained at room temperature
  3. stirringthe resulting mixture was stirred
  4. temperaturewhile being maintained at room temperature
  5. concentrationwas then concentrated to dryness
  6. customThe resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=10/1/0.1)

Sources & evidence

ORD record
ord-9823f3dd397e4225b2df29063933921c
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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