Tetrahydro-2-furoic acid, (+)- → ((R)-3-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YLAMINO}-PYRROLIDIN-1-YL)-(R)-TETRAHYDRO-FURAN-2-YL-METHANONE

HRID 70116

Reaction equation

HRID 70116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16]([NH:24][C@@H:25]4[CH2:29][CH2:28][NH:27][CH2:26]4)[C:17]4[S:22](=[O:23])[CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:30]1[CH2:34][CH2:33][CH2:32][C@@H:31]1[C:35](O)=[O:36]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[N:15]=[C:16]([NH:24][C@@H:25]4[CH2:29][CH2:28][N:27]([C:35]([C@H:31]5[CH2:32][CH2:33][CH2:34][O:30]5)=[O:36])[CH2:26]4)[C:17]4[S:22](=[O:23])[CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 59708374{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-(R)-pyrrolidin-3-yl-amine

Product 1

HCID 59708375((R)-3-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YLAMINO}-PYRROLIDIN-1-YL)-(R)-TETRAHYDRO-FURAN-2-YL-METHANONE

Procedure

Starting from {2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl}-(R)-pyrrolidin-3-yl-amine Diastereomer 1 (Example 171) (see scheme 3, 3.22) and (R)-(+)-tetrahydrofuran-2-carboxylic acid, Example 196 is prepared as described in Example 231 (see scheme 7). The product is purified by preparative HPLC (method B). Analytical HPLC-MS (method D): RT=1.18 min.

Workup

  1. customis prepared
  2. customThe product is purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-f336a39b66004c97bf8c7074cb184f2a
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Linked notes

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