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Hydrochloric Acid → 3-{3,5-Dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid

HRID 1514958
Notes
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Reaction equation

HRID 1514958 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([C:22](=[O:34])[NH:23][C:24]2[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=2)[CH:16]=3)=[C:8]([CH3:35])[CH:7]=1.O.[OH-].[Li+].C1COCC1.CO.O.Cl>O>[CH3:12][C:10]1[CH:11]=[C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])[CH:7]=[C:8]([CH3:35])[C:9]=1[C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22](=[O:34])[NH:23][C:24]1[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=1)[CH:16]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 669656943-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid methyl ester

Product 1

HCID 669650393-{3,5-Dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid methyl ester (100 mg, 210 μmol) and lithium hydroxide monohydrate (26 mg, 620 μmol) in 5:5:2 THF/MeOH/H2O (10 mL) was stirred at ambient temperature for 18 h. The solution was concentrated to remove the organic solvents, then was diluted with water and neutralized with one equivalent of 1N HCl. The mixture was stirred vigorously for 30 min and the precipitate was filtered and washed with water. The solid was triturated with water and refiltered, then dried at 50° C. under reduced pressure to give the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.15 (s, broad, 1H), 11.56 (s, 1H), 10.99 (s, 1H), 8.39 (s, 2H), 8.16 (s, 1H), 7.95 (d, J=7.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 7.79 (dd, J=8.3, 1.4 Hz, 1H), 7.73 (m, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.52 (t, J=7.1 Hz, 1H), 7.06 (s, 2H), 6.41 (d, J=1.4 Hz, 1H), 2.82 (t, J=7.4 Hz, 2H), 2.57 (t, J=7.6 Hz, 2H), 2.11 (s, 6H). MS (m/z) 464.3 (M+1); Retention time=1.36 min (Method 10).

Workup

  1. concentrationThe solution was concentrated
  2. customto remove the organic solvents
  3. stirringThe mixture was stirred vigorously for 30 min
  4. filtrationthe precipitate was filtered
  5. washwashed with water
  6. customThe solid was triturated with water
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-7b11d905541a46729c889ee5305301ea
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08222248B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes