Isopropyl isocyanate → 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid isopropylamide

HRID 2064620Notes

Reaction equation

HRID 2064620 reaction equation
[CH3:1][C:2]1[C:19]([CH3:20])=[CH:18][C:5]2[NH:6][C:7]([C:9]3[C:13]4[CH2:14][NH:15][CH2:16][CH2:17][C:12]=4[NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH:21]([N:24]=[C:25]=[O:26])([CH3:23])[CH3:22]>>[CH:21]([NH:24][C:25]([N:15]1[CH2:16][CH2:17][C:12]2[NH:11][N:10]=[C:9]([C:7]3[NH:6][C:5]4[CH:18]=[C:19]([CH3:20])[C:2]([CH3:1])=[CH:3][C:4]=4[N:8]=3)[C:13]=2[CH2:14]1)=[O:26])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 61277Isopropyl isocyanateHCID 1358045913-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1359003323-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid isopropylamide

Procedure

By proceeding in a manner similar to Example 255(a) above but using 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [Example 251(a)] and isopropylisocyanate, and subjecting the reaction product to flash column chromatography eluting with ethyl acetate/methanol (19:1, v/v), there was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid isopropylamide (93.3 mg) as an off-white solid. LC-MS (METHOD M): RT=10.15 minutes, 353 (M+H)+.

Workup

  1. washeluting with ethyl acetate/methanol (19:1
  2. customv/v), there was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid isopropylamide (93.3 mg) as an off-white solid

Sources & evidence

ORD record
ord-0a788e301fe44b0fa75a93b8741ad720
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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