Methylamine → 7-(2-Methoxyethoxy)-N-(1-(3-(methylcarbamoyl)benzyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706673Notes

Reaction equation

HRID 706673 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[CH2:27][C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=3)[C:31](OC)=[O:32])=[O:16])=[CH:13][N:14]=[C:8]2[CH:7]=1.[CH3:38][NH2:39]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[CH2:27][C:28]3[CH:37]=[CH:36][CH:35]=[C:30]([C:31](=[O:32])[NH:39][CH3:38])[CH:29]=3)=[O:16])=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 57384340HCID 57384340, compound

Product 1

HCID 573846007-(2-Methoxyethoxy)-N-(1-(3-(methylcarbamoyl)benzyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 54%

Conditions

Temperature
50 °C

Procedure

To a vial was added methyl 3-((4-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)benzoate (Example 93; 0.026 g, 0.0521 mmol) followed by methylamine (0.972 mL, 7.81 mmol, 33% in EtOH) and the mixture was sealed and heated to 50° C. with stirring for 8 hours. Additional methyl amine (0.972 mL, 7.81 mmol) was added and the mixture was stirred at 50° C. overnight. The mixture was cooled to ambient temperature and purified directly by preparative TLC (10% MeOH/CH2Cl2), providing 0.014 g (54%) of the product as a tan powder. MS (ES+APCI) m/z=499 (M+H).

Workup

  1. customthe mixture was sealed
  2. stirringthe mixture was stirred at 50° C. overnight
  3. temperatureThe mixture was cooled to ambient temperature
  4. custompurified directly by preparative TLC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c3a3598f5f9e45b8b6de9e51103aa375
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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