Hydrochloric Acid → HCID 53912738, compound

HRID 273868Notes

Reaction equation

HRID 273868 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][C@H:16]([NH:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.C(=O)(O)[O-:36].[Na+]>C(O)(C)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][C@H:16]([NH:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH2:29][C:30]([F:33])([F:31])[F:32])[CH3:17])=[CH:10][C:11]=2[C:13]([NH2:14])=[O:36])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 54280378HCID 54280378, compound

Product 1

HCID 53912738HCID 53912738, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (R)-(-)-1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile (2.00 g) in isopropanol (4.2 ml) was added concentrated hydrochloric acid (4.2 ml) slowly with stirring under ice cooling, and the mixture was stirred for 40 minutes. The reaction mixture was neutralized by a saturated aqueous sodium bicarbonate solution, and extracted with methylene chloride. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1.70 g of (R)-(-)-1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carboxamide melting at 144°-146° C.

Workup

  1. stirringthe mixture was stirred for 40 minutes
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aef8e19cc814440e8ce2026aa9b540b4
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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