[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamine → 6'-[2-allyl-6-({4-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]phenyl}amino)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

HRID 2191907Notes

Reaction equation

HRID 2191907 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[CH:4][CH:3]=1.[CH2:16]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[N:22][C:23](SC)=[N:24][CH:25]=2)[N:20]1[C:31]1[N:36]=[C:35]([N:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]2=[O:43])[CH:34]=[CH:33][CH:32]=1)[CH:17]=[CH2:18]>>[CH2:16]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[N:22][C:23]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]4)=[CH:4][CH:3]=3)=[N:24][CH:25]=2)[N:20]1[C:31]1[N:36]=[C:35]([N:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]2=[O:43])[CH:34]=[CH:33][CH:32]=1)[CH:17]=[CH2:18]

Participants

3

Reactant 2

HCID 59815627[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamineHCID 684275366'-[2-allyl-6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Product 1

HCID 426027646'-[2-allyl-6-({4-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]phenyl}amino)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Procedure

The entitled compound was obtained as a yellow solid (35.5 mg) in the same manner as in Production Example 12-2, for which, however, (3R)-1-(4-aminophenyl)-N,N-dimethylpyrrolidin-3-amine was used in place of [5-amino-2-(4-methylpiperazin-1-yl)phenyl]methanol used in Production Example 12-2, and 6′-[2-allyl-6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2′-bipyridin-2-one was used in place of 2-allyl-6-(methylthio)-1-pyridin-2-yl-3H-pyrazolo[3,4-d]pyrimidin-3-one.

Sources & evidence

ORD record
ord-f3fd58e4cc70416c9e7a13068b49c867
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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