Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate → 2-(6-Fluoro-1H-indol-4-yl)-6-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066555Notes

Reaction equation

HRID 2066555 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([C:11]2[N:12]=[C:13]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:14]3[S:19][C:18]([CH2:20][N:21]4[CH2:26][C@@H]5CCCN5C[CH2:22]4)=[CH:17][C:15]=3[N:16]=2)[CH:3]=1.C(OC([N:43]1[CH2:50][CH:49]2[CH:45](CNC2)[CH2:44]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([C:11]2[N:12]=[C:13]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:14]3[S:19][C:18]([CH2:20][N:21]4[CH2:22][CH:49]5[CH:45]([CH2:44][NH:43][CH2:50]5)[CH2:26]4)=[CH:17][C:15]=3[N:16]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 581170432-(6-fluoro-1H-indol-4-yl)-6-[(5)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno-[3,2-d]pyrimidine

Product 1

HCID 462398962-(6-Fluoro-1H-indol-4-yl)-6-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Procedure

Prepared according to the method used in the preparation of 2-(6-fluoro-1H-indol-4-yl)-6-[(S)-1-(hexahydro-pyrrolo[1,2-d]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno-[3,2-d]pyrimidine using hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester in place of (S)-octahydro-pyrrolo[1,2-a]pyrazine, followed by BOC-deprotection using TFA:DCM (1:1). The title compound was obtained as a white solid (34 mg, 47%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-25f26a6a9b384b0c9c0f99131453759a
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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