Aniline → (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-Pyridin-2yl)-benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one

HRID 1182669Notes

Reaction equation

HRID 1182669 reaction equation
Cl[C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:22][CH:21]=2)[CH:4]=[C:5]2[N:10]3[C@H:11]4[CH2:16][CH2:15][CH2:14][C@H:12]4[N:13]=[C:9]3[N:8]([CH3:17])[C:7](=[O:18])[C:6]=12.[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:17][N:8]1[C:7](=[O:18])[C:6]2=[C:2]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:3]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:24][CH:25]=3)[CH:4]=[C:5]2[N:10]2[C@H:11]3[CH2:16][CH2:15][CH2:14][C@H:12]3[N:13]=[C:9]12

Participants

3

Reactant 2

HCID 6115AnilineHCID 46830563HCID 46830563, compound

Product 1

HCID 46834597(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-Pyridin-2yl)-benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one

Conditions

Temperature
150 °C

Procedure

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-3-chloro-5-methyl-2-((4-Pyridin-2yl)-benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one (5.6 mg, 0.013 mmol) is placed in a Biotage microwave tube, and then aniline (0.2 mL) is added. The mixture is heated at 150° C. for an hour. The mixture is purified by a semi-preparative HPLC to give product. MS (ESI) m/z 489.3 [M+H]+.

Workup

  1. customThe mixture is purified by a semi-preparative HPLC
  2. customto give product

Sources & evidence

ORD record
ord-c33e1b8e83d141a9af7aab5b1fb0cd43
Source dataset
uspto-grants-2014_03
Patent number
US08664207B2

Reaction notes

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