Picolyl chloride → 4-Chloro-3-methyl-1-(2-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinoline

HRID 497974Notes

Reaction equation

HRID 497974 reaction equation
O=[C:2]([CH3:15])[CH2:3][C:4]1O[C:8](=O)[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1.[NH:16]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[NH2:17].[Cl:25]CC1C=CC=CN=1>>[Cl:25][C:8]1[C:7]2[C:6](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]2[N:16]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:17]=[C:2]([CH3:15])[C:3]=12

Participants

4

Reactant 3

HCID 23393Picolyl chlorideHCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-oneHCID 162287212-(Hydrazinylmethyl)pyridine

Product 1

HCID 223201004-Chloro-3-methyl-1-(2-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinoline

Procedure

Following the procedures described in Reference Example 1-10 and Example 1-34, the title compound was prepared from 2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one and 2-hydrazinomethylpyridine which was separately prepared from 2-chloromethylpyridine following the method described in Reference Example 1-9 (75% yield).

Sources & evidence

ORD record
ord-fd12e5214e954f5f8bd114daae15d1bd
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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