1,1'-Carbonyldiimidazole → 4-(4-Chlorophenyl)piperidine-1-carboxylic acid [4-(5-methylhexahydropyrrolo[3,4-b]pyrrol-1-yl)phenyl]amide

HRID 1174709Notes

Reaction equation

HRID 1174709 reaction equation
CN1CC2C(NCC2)C1.[CH3:10][N:11]1[CH2:18][CH:17]2[CH:13]([N:14]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[CH2:15][CH2:16]2)[CH2:12]1.[C:26]([N:33]1[CH:37]=[CH:36]N=[CH:34]1)(N1C=CN=C1)=[O:27].[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2CCNC[CH2:46]2)=[CH:41][CH:40]=1>>[CH3:10][N:11]1[CH2:18][CH:17]2[CH:13]([N:14]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:33]4[CH2:34][CH2:46][CH:45]([C:42]5[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=5)[CH2:36][CH2:37]4)=[O:27])=[CH:21][CH:20]=3)[CH2:15][CH2:16]2)[CH2:12]1

Participants

5

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 12036134-(4-Chlorophenyl)piperidineHCID 162288995-Methyl-octahydropyrrolo(3,4-b)pyrroleHCID 68427891HCID 68427891, compound

Product 1

HCID 730412324-(4-Chlorophenyl)piperidine-1-carboxylic acid [4-(5-methylhexahydropyrrolo[3,4-b]pyrrol-1-yl)phenyl]amide

Procedure

5-Methyloctahydropyrrolo[3,4-b]pyrrole (EP 0 393 424) was initially converted as described in Example 3 into 4-(5-methylhexahydropyrrolo[3,4-b]pyrrol-1-yl)-phenylamine and then reacted with carbonyldiimidazole and subsequently with 4-(4-chlorophenyl)piperidine. The product with the molecular weight of 439.01 (C25H31ClN4O); MS (ESI): 439 (M+H+) was obtained in this way.

Workup

  1. customMS (ESI): 439 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-3d318bd4c28048da88fc747506d4f6a9
Source dataset
uspto-grants-2010_11
Patent number
US07838547B2

Reaction notes

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