Sodium Hydroxide → HCID 44612507, compound

HRID 1645732Notes

Reaction equation

HRID 1645732 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([C:28](=[O:37])[NH:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[NH2:36])=[CH:24][CH:23]=4)[N:16]=3)=[C:12]([CH3:14])[N:13]=[C:7]2[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[NH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:17]2[N:16]=[C:15]([C:11]3[N:8]4[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]4=[N:13][C:12]=3[CH3:14])[CH:20]=[CH:19][N:18]=2)=[CH:27][CH:26]=1)=[O:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44612390HCID 44612390, compound

Product 1

HCID 44612507HCID 44612507, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 3-{2-[4-(2-amino-phenylcarbamoyl)-phenylamino]-pyrimidin-4-yl}-2-methyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (200 mg, 0.4 mmol) was dissolved in MeOH (5 mL) and then treated with 1N NaOH (1 mL). After 2 hours the reaction mixture was evaporated and the solids were re-suspended in water and 1N HCl was slowly added to precipitate the title compound. MS found for C26H21N7O3 as (M+H)+ 480.53. 1H NMR (400 MHz, dmso-d6): δ 9.99 (s, 1H), 9.72 (d, J=5.6 Hz, 1H), 9.47 (s, 1H), 8.59 (d, J=5.5 Hz, 1H), 8.07 (s, 1H), 7.90-7.84 (m, 4H), 7.39 (dd, J=7.2, 6.0 Hz, 1H), 7.18-7.09 (m, 2H), 6.90 (t, J=6.0 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.56-6.48 (m, 1H), 2.64 (s, 3H).

Workup

  1. customAfter 2 hours the reaction mixture was evaporated
  2. addition1N HCl was slowly added
  3. customto precipitate the title compound

Sources & evidence

ORD record
ord-1aace48c0c974561b23f8b30a3924d06
Source dataset
uspto-grants-2012_02
Patent number
US08124764B2

Reaction notes

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