3-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-one → 1-[[(7S)-4-chloro-9-(2,2-dimethylpropyl)-3,6,7,8,9,10-hexahydro-8-oxoazepino[3,4-e]indazol-7-yl]acetyl]-4-(1,2-dihydro-2-oxo-1,6-naphthyridin-3-yl)-piperidine

HRID 132497Notes

Reaction equation

HRID 132497 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8](=[O:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][N:13]=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.[Cl:18][C:19]1[C:27]2[NH:26][N:25]=[CH:24][C:23]=2[C:22]2[CH2:28][N:29]([CH2:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:30](=[O:53])[C@@H:31]([CH2:33][C:34](=[O:52])N3CCC(N4CC5C(=CC=CC=5)NC4=O)CC3)[CH2:32][C:21]=2[CH:20]=1>>[Cl:18][C:19]1[C:27]2[NH:26][N:25]=[CH:24][C:23]=2[C:22]2[CH2:28][N:29]([CH2:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:30](=[O:53])[C@H:31]([CH2:33][C:34]([N:1]3[CH2:2][CH2:3][CH:4]([C:7]4[C:8](=[O:17])[NH:9][C:10]5[C:15]([CH:16]=4)=[CH:14][N:13]=[CH:12][CH:11]=5)[CH2:5][CH2:6]3)=[O:52])[CH2:32][C:21]=2[CH:20]=1

Participants

3

Reactant 2

HCID 597319443-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-oneHCID 688264794-Chloro-9-(2,2-dimethyl-propyl)-7-(R)-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one

Product 1

HCID 119790161-[[(7S)-4-chloro-9-(2,2-dimethylpropyl)-3,6,7,8,9,10-hexahydro-8-oxoazepino[3,4-e]indazol-7-yl]acetyl]-4-(1,2-dihydro-2-oxo-1,6-naphthyridin-3-yl)-piperidineYield 27%

Procedure

3-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-one (89 mg, 0.29 mmol) and [4-chloro-9-(2,2-dimethyl-propyl)-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-(S)-cyclohepta[e]inden-7-yl]acetic acid (95 mg, 0.26 mmol) were combined in a manner analogous to the preparation of 4-Chloro-9-(2,2-dimethyl-propyl)-7-(R)-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one. Title compound was obtained as white solid in 27% yield. High resolution MS m/e (M+H)+=575.2538.

Sources & evidence

ORD record
ord-ab11a9305b73490396cc4c0fd1c4749b
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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