Diethylcarbamoyl chloride → 3-(5-Chloro-6-methyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid diethylamide
Reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([N:6]1[CH2:11][CH2:10][C:9]2[NH:12][N:13]=[C:14]([C:15]3[NH:19][C:18]4[CH:20]=[C:21]([CH3:25])[C:22](C)=[CH:23][C:17]=4[N:16]=3)[C:8]=2[CH2:7]1)=[O:5])[CH3:2].[Cl:28]C1C(C)=CC2NC(C3C4CNCCC=4NN=3)=NC=2C=1.C(N(CC)C(Cl)=O)C>>[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([N:6]1[CH2:11][CH2:10][C:9]2[NH:12][N:13]=[C:14]([C:15]3[NH:19][C:18]4[CH:20]=[C:21]([CH3:25])[C:22]([Cl:28])=[CH:23][C:17]=4[N:16]=3)[C:8]=2[CH2:7]1)=[O:5])[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
By proceeding in a manner similar to Example 258(a) above but (i) using 3-(5-chloro-6-methyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine [Example 251(b)] and diethylcarbamyl chloride, and (ii) subjecting the reaction product to flash column chromatography, eluting with ethyl acetate to ethyl acetate/methanol (47:3, v/v) followed by trituration with ethanol, there was prepared 3-(5-chloro-6-methyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid diethylamide (35.6 mg) as a pale yellow solid. MS: 387/389 (M+H)+. HPLC (METHOD E1): RT=11.07 minutes.
Workup
- washeluting with ethyl acetate to ethyl acetate/methanol (47:3
- customwas prepared 3-(5-chloro-6-methyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid diethylamide (35.6 mg) as a pale yellow solid
Sources & evidence
- ORD record
- ord-799e4ee97bed4deb8854f20d6ec54a9b
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288425B2
Reaction notes
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