1-Methylpiperazin-2-one → {(S)-6-[(R)-4-(4-Methyl-3-oxo-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

HRID 1422639Notes

Reaction equation

HRID 1422639 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:28][N:29]5[CH2:34][CH2:33][N:32]([CH3:35])[C:31](=[O:36])[CH2:30]5)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.COC(=O)C[C@H]1C2C=CC(O[C@H]3C4C(=C(CBr)C(C(F)(F)F)=CC=4)CC3)=CC=2OC1.CN1CCNCC1=O>>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([CH2:28][C:19]2[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=[C:23]3[C:18]=2[CH2:17][CH2:16][C@H:15]3[O:14][C:12]2[CH:11]=[CH:10][C:9]3[C@H:5]([CH2:4][C:3]([OH:37])=[O:2])[CH2:6][O:7][C:8]=3[CH:13]=2)[CH2:30][C:31]1=[O:36]

Participants

4

Reactant 3

HCID 43990421-Methylpiperazin-2-oneHCID 86700813{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 90314425{(S)-6-[(R)-4-(4-methyl-3-oxo-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90313819{(S)-6-[(R)-4-(4-Methyl-3-oxo-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

Procedure

The methyl ester of the title compound, {(S)-6-[(R)-4-(4-methyl-3-oxo-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester, is prepared from {(S)-6-[(R)-4-bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and 1-methyl-piperazin-2-one following a procedure analogous to that described for Intermediate 42. The crude product is directly submitted to the saponification conditions described for Example 1 to give the title compound upon chromatography on reversed phase (HPLC; acetonitrile/water). LC (method 6): tR=1.03 min; Mass spectrum (ESI+): m/z=505 [M+H]+.

Sources & evidence

ORD record
ord-749bb1dfad3e422d9e9bbf9d1d5d545e
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

Loading…