2-Indancarboxylic Acid → 4-[2-(S)-Methyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid

HRID 2110143Notes

Reaction equation

HRID 2110143 reaction equation
C1C2C(=CC=CC=2)CC1C(O)=O.[CH3:13][C@@H:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)[CH2:15]1.C[O:32][C:33]([CH:35]1[CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[S:44](Cl)(=[O:46])=[O:45])[CH2:36]1)=[O:34]>>[CH3:13][C@H:14]1[CH2:15][N:16]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:17][CH2:18][N:19]1[S:44]([C:41]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:42]=1[CH2:43][CH:35]([C:33]([OH:34])=[O:32])[CH2:36]2)(=[O:46])=[O:45]

Participants

4

Reactant 3

HCID 5757772-Indancarboxylic AcidHCID 46835233methyl 4-(chlorosulfonyl)-2,3-dihydro-1H-indene-2-carboxylateHCID 670459573-(S)-methyl-1-(4-trifluoromethoxy-phenyl)-piperazine

Product 1

HCID 575652924-[2-(S)-Methyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid

Procedure

4-|2-(S)-Methyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl|-indan-2-carboxylic acid. The compound 4-[2-(S)-Methyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid was prepared from 3-(S)-methyl-1-(4-trifluoromethoxy-phenyl)-piperazine and 4-chlorosulfonyl-indan-2-carboxylic acid methyl ester following the procedure outlined in Example 79. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1H), 7.53 (d, 1H), 7.38 (t, 1H), 7.18 (d, 2H), 6.98-6.92 (m, 2H), 4.15-4.00 (m, 1H), 3.60-3.12 (m, 9H), 2.83-2.75 (m, 1H), 2.64-2.50 (m, 1H), 1.18 (d, 3H); MS (ESI): 485.3 (M+H).

Sources & evidence

ORD record
ord-30274f362cf9450e96da4d2a99eb6199
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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