2-Indancarboxylic Acid → 4-[2-(S)-Methyl-4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid

HRID 2110144Notes

Reaction equation

HRID 2110144 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]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=2)[CH2:15]1.C[O:31][C:32]([CH:34]1[CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][C:40]=2[S:43](Cl)(=[O:45])=[O:44])[CH2:35]1)=[O:33]>>[CH3:13][C@H:14]1[CH2:15][N:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][N:21]=2)[CH2:17][CH2:18][N:19]1[S:43]([C:40]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:41]=1[CH2:42][CH:34]([C:32]([OH:33])=[O:31])[CH2:35]2)(=[O:45])=[O:44]

Participants

4

Reactant 3

HCID 5757772-Indancarboxylic AcidHCID 26597362(S)-3-methyl-1-(5-(trifluoromethyl)pyridin-2-yl)piperazineHCID 46835233methyl 4-(chlorosulfonyl)-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 576359744-[2-(S)-Methyl-4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid

Procedure

4-|2-(S)-Methyl-4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl|-indan-2-carboxylic acid. The compound 4-[2-(S)-Methyl-4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid was prepared from 3-(S)-methyl-1-(5-trifluoromethyl-pyridin-2-yl)-piperazine and 4-chlorosulfonyl-indan-2-carboxylic acid methyl ester following the procedure outlined in Example 79. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (s, 1H), 7.82-7.76 (m, 1H), 7.65 (d, 1H), 7.52 (d, 1H), 7.37 (t, 1H), 6.93-6.88 (m, 1H), 4.35-4.18 (m, 2H), 4.18-4.02 (m, 1H), 3.60-3.46 (m, 1H), 3.45-3.10 (m, 7H), 2.97-2.80 (m, 1H), 1.06-1.01 (m, 3H); MS (ESI): 470.0 (M+H).

Sources & evidence

ORD record
ord-9be33ef05f2c47dc9de34a48b39e488f
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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