Racemic trans-(3-methoxy-cyclopentyl)-acetic acid methyl ester → HCID 178496557, compound

HRID 2042423Notes

Reaction equation

HRID 2042423 reaction equation
Cl.Cl.Cl.[S:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1.C[O:29][C:30](=O)[CH2:31][C@H:32]1[CH2:36][CH2:35][C@H:34]([O:37][CH3:38])[CH2:33]1>>[CH3:38][O:37][C@H:34]1[CH2:35][CH2:36][C@H:32]([CH2:31][C:30]([NH:27][C@H:24]2[CH2:25][CH2:26][C@H:21]([CH2:20][CH2:19][N:16]3[CH2:17][CH2:18][N:13]([C:8]4[C:7]5[CH:6]=[CH:5][S:4][C:12]=5[CH:11]=[CH:10][N:9]=4)[CH2:14][CH2:15]3)[CH2:22][CH2:23]2)=[O:29])[CH2:33]1

Participants

3

Reactant 2

HCID 59598533Racemic trans-(3-methoxy-cyclopentyl)-acetic acid methyl esterHCID 178478593HCID 178478593, compound2×

Product 1

HCID 178496557HCID 178496557, compound

Procedure

The title compound was prepared in analogy to example 2 starting from trans-4-[2-(4-thieno[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine trihydrochloride (intermediate B) (100 mg, 0.22 mmol) and racemic trans-(3-methoxy-cyclopentyl)-acetic acid methyl ester [WO 2009/019174] (46 mg, 0.27 mmol). Purification by flash chromatography on silica gel (CH2Cl2/MeOH 95:5). White crystals (61 mg, 57%), MS (ISP) m/z=485.4 [(M+H)+].

Workup

  1. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-6ad4acb5e35d406a90213184c4f48a05
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

Loading…