Dimethylamine, hydrochloride → 3-(5,6-Dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid dimethylamide dihydrochloride
Reaction equation
[N:1]1[CH:6]=CC=C(CNC(C2C=CC3NC(C4C(C(=O)NC(C)C)=CNN=4)=NC=3C=2)=O)[CH:2]=1.[CH3:31][C:32]1[C:52]([CH3:53])=[CH:51][C:35]2[NH:36][C:37]([C:39]3[C:47]4[C:42](=[CH:43][CH:44]=[C:45]([C:48]([OH:50])=O)[CH:46]=4)[NH:41][N:40]=3)=[N:38][C:34]=2[CH:33]=1.[ClH:54].CNC>>[ClH:54].[ClH:54].[CH3:2][N:1]([CH3:6])[C:48]([C:45]1[CH:46]=[C:47]2[C:42](=[CH:43][CH:44]=1)[NH:41][N:40]=[C:39]2[C:37]1[NH:38][C:34]2[CH:33]=[C:32]([CH3:31])[C:52]([CH3:53])=[CH:51][C:35]=2[N:36]=1)=[O:50]Participants
4
Procedure
By proceeding in a manner similar to Example 246(j) above, but (i) using 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid [97 mg, Example 263] and dimethylamine hydrochloride (23 mg), (ii) carrying out the reaction at ambient temperature overnight, and (iii) subjecting the reaction product to flash column chromatography [eluting with ethyl acetate to ethyl acetate/methanol (97:3, v/v)] followed by treatment with 4M hydrogen chloride in 1,4-dioxane and trituration with dichloromethane and diethyl ether there was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid dimethylamide dihydrochloride (8 mg) as a white solid. LC-MS (METHOD M): RT=9.37 minutes, 320 (M+H)+.
Workup
- washeluting with ethyl acetate to ethyl acetate/methanol (97:3
- customthere was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazole-5-carboxylic acid dimethylamide dihydrochloride (8 mg) as a white solid
Sources & evidence
- ORD record
- ord-05638f5093514d728d1608107c0a94f9
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288425B2
Reaction notes
Loading…