(2S)-1-(2,3,5,6-Tetrafluorophenyl)propan-2-amine → (S)-6-(1-Methylpiperidin-4-yl)-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69340Notes

Reaction equation

HRID 69340 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH2:11][C@@H:12]([NH2:14])[CH3:13].Cl[C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[C:17]=1[C:23]1[NH:43][C:26]2=[CH:27][C:28]3[C:29](=[O:42])[N:30]([CH:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)[C:31](=[O:34])[C:32]=3[CH:33]=[C:25]2[N:24]=1>>[CH3:41][N:38]1[CH2:39][CH2:40][CH:35]([N:30]2[C:29](=[O:42])[C:28]3[CH:27]=[C:26]4[NH:43][C:23]([C:17]5[C:18](=[O:22])[NH:19][CH:20]=[CH:21][C:16]=5[NH:14][C@@H:12]([CH3:13])[CH2:11][C:3]5[C:2]([F:1])=[C:7]([F:8])[CH:6]=[C:5]([F:9])[C:4]=5[F:10])=[N:24][C:25]4=[CH:33][C:32]=3[C:31]2=[O:34])[CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 86663212(2S)-1-(2,3,5,6-Tetrafluorophenyl)propan-2-amineHCID 1362002202-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-(1-methylpiperidin-4-yl)-imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 136340639(S)-6-(1-Methylpiperidin-4-yl)-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Procedure

(S)-1-(2,3,5,6-Tetrafluorophenyl)propan-2-amine and 2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione were submitted to general procedure A. The isolated solid was triturated with water once and MeOH four times to give the title compound as an off-white solid, which was used directly in the next step.

Workup

  1. customThe isolated solid was triturated with water once

Sources & evidence

ORD record
ord-9659cda79fbe43fcb829eb482fe34f6e
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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