Hydrogen chloride-ethyl acetate → HCID 66868409, compound

HRID 1909888Notes

Reaction equation

HRID 1909888 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:24]=2[N:23]([CH2:25][CH:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]2)[CH:22]=[CH:21]3)=[O:15])[CH3:12])=[CH:7][CH:6]=1)=[O:4].C(OC(=O)C)C.[ClH:45]>C1COCC1>[ClH:45].[NH:29]1[CH2:28][CH2:27][CH:26]([CH2:25][N:23]2[C:24]3[C:20](=[CH:19][CH:18]=[CH:17][C:16]=3[C:14]([NH:13][C@H:11]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=3)[CH3:12])=[O:15])[CH:21]=[CH:22]2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58306890HCID 58306890, compound

Product 1

HCID 66868409HCID 66868409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 4-{[7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)-1H-indol-1-yl]methyl}piperidine-1-carboxylate (1.67 g), and THF (20 mL) was added a 4 M hydrogen chloride ethyl acetate solution (2.0 mL) at room temperature, followed by stirring for 1 hour. The reaction mixture was stirred at 60° C. for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was washed with ethyl acetate and diethyl ether, collected by filtration, and dried under reduced pressure to obtain methyl 4-[(1S)-1-({[1-(piperidin-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate hydrochloride (1.46 g).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 6 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washThe residue was washed with ethyl acetate and diethyl ether
  4. filtrationcollected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d4f25544d09485193004eab38a42076
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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