Water → 1H-Indole-7-carbonitrile, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]-

HRID 1173782Notes

Reaction equation

HRID 1173782 reaction equation
C(O)(=O)C(O)=[O:3].C([O:15][CH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:30][C@H:31]([NH:33][CH2:34][CH2:35][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH2:44][C:45]([F:48])([F:47])[F:46])[CH3:32])=[CH:25][C:26]=2[C:28]#[N:29])[CH2:21][CH2:20]1)(=O)C1C=CC=CC=1.[OH-].[K+:50].O>CO>[OH-:3].[K+:50].[OH:15][CH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:30][C@H:31]([NH:33][CH2:34][CH2:35][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH2:44][C:45]([F:48])([F:46])[F:47])[CH3:32])=[CH:25][C:26]=2[C:28]#[N:29])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 66713997Oxalic acid--3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate (1/1)

Product 2

HCID 14797Potassium HydroxideHCID 115330471H-Indole-7-carbonitrile, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]-Yield 110.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{7-Cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}-propyl benzoate monooxalate(10.0 g) was dissolved. in methanol (40 mL), then an aqueous potassium hydroxide solution, which was prepared from potassium hydroxide (2.93 g) and water (10 mL) was added little by little, and the mixture was stirred at room temperature for overnight. To the reaction mixture, water (150 mL) was added and extracted with ethyl acetate (150 mL and 50 mL) successively. The combined ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure to give 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]-ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (7.86 g).

Workup

  1. additionwas added little by little, and the mixture
  2. extractionextracted with ethyl acetate (150 mL and 50 mL) successively
  3. washThe combined ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88990c9b29044f32b5e69935dfa06a40
Source dataset
uspto-grants-2010_11
Patent number
US07834193B2

Reaction notes

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