Propionyl chloride → {(S)-6-[(R)-4-(4-Propionyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422624Notes

Reaction equation

HRID 1422624 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH3:6][O:7][C:8](=[O:40])[CH2:9][C@H:10]1[C:14]2[CH:15]=[CH:16][C:17]([O:19][C@H:20]3[C:28]4[C:23](=[C:24]([CH2:33][N:34]5[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]5)[C:25]([C:29]([F:32])([F:31])[F:30])=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)=[CH:18][C:13]=2[O:12][CH2:11]1>N1C=CC=CC=1>[CH3:6][O:7][C:8](=[O:40])[CH2:9][C@H:10]1[C:14]2[CH:15]=[CH:16][C:17]([O:19][C@H:20]3[C:28]4[C:23](=[C:24]([CH2:33][N:34]5[CH2:35][CH2:36][N:37]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:38][CH2:39]5)[C:25]([C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)=[CH:18][C:13]=2[O:12][CH2:11]1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 90313619{(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90312787{(S)-6-[(R)-4-(4-Propionyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound is prepared from propionyl chloride and {(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester following a procedure analogous to that described for Intermediate 27; pyridine instead of triethylamine is used. LC (method 4): tR=0.97 min; Mass spectrum (ESI+): m/z=547 [M+H]+.

Sources & evidence

ORD record
ord-92f59a8cf6fb4e2e9413b53ac73a1a6a
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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