6-Chloroquinoline-4-carbaldehyde → tert-butyl 4-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-methyl-1,3-thiazol-2-ylcarbamate

HRID 1181784Notes

Reaction equation

HRID 1181784 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10]([NH:11][NH2:12])=[CH:9][C:8](=[O:13])[N:7]([CH3:14])[C:6]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[C:20]2[CH:27]=O.[CH:29]([C:31]1[N:32]=[C:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[S:34][C:35]=1[CH3:36])=O>>[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[C:20]2[CH2:27][N:12]1[C:29]([C:31]2[N:32]=[C:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[S:34][C:35]=2[CH3:36])=[C:9]2[C:10]([N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:6](=[O:15])[N:7]([CH3:14])[C:8]2=[O:13])=[N:11]1

Participants

4

Reactant 3

HCID 31460316-Chloroquinoline-4-carbaldehydeHCID 694271711-(cyclopropylmethyl)-6-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dioneHCID 87831662HCID 87831662, compound

Product 1

HCID 86595428tert-butyl 4-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-methyl-1,3-thiazol-2-ylcarbamate

Procedure

This compound was made following the procedure described above, starting with 1-(cyclopropylmethyl)-6-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dione, and condensing first with 6-chloroquinoline-4-carbaldehyde, followed by tert-butyl 4-formyl-5-methyl-1,3-thiazol-2-ylcarbamate.

Sources & evidence

ORD record
ord-bfb750bff592486db61f0226d909c45e
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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