Bromoacetonitrile → [2-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-3-(4-methyl-4H-1,2,4-triazol-3-yl)-4,6-dioxo-2,4,6,7-tetrahydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl]acetonitrile

HRID 1181839Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[N:24][N:23]=2)=[C:20]2[C:15]([N:16]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:17](=[O:29])[NH:18][C:19]2=[O:28])=[N:14]1.Br[CH2:35][C:36]#[N:37]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[N:24][N:23]=2)=[C:20]2[C:15]([N:16]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:17](=[O:29])[N:18]([CH2:35][C:36]#[N:37])[C:19]2=[O:28])=[N:14]1

Participants

Reactant 2

HCID 11534Bromoacetonitrile

HCID 589810832-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-3-(4-methyl-4H-1,2,4-triazol-3-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 58980901[2-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-3-(4-methyl-4H-1,2,4-triazol-3-yl)-4,6-dioxo-2,4,6,7-tetrahydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl]acetonitrile

Procedure

This compound was made by alkylation of 2-[(6-chloroquinolin-4-yl)methyl]-7-isobutyl-3-(4-methyl-4H-1,2,4-triazol-3-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione with bromoacetonitrile following conditions in Example 6.d. 504.2 (M+H).

Sources & evidence

ORD record: ord-3268ff9a10ae49acb4e1a72f2b51b440
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285558B2

Reaction notes

Loading…