Trifluoroacetic acid → HCID 69056946, compound

HRID 1984302Notes

Reaction equation

HRID 1984302 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10]1)C)(C)(C)C.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[NH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[C:16]1[C:14]([N:11]1[CH2:12][CH2:13][CH:9]([NH:7][CH3:6])[CH2:10]1)=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69058821HCID 69058821, compound

Product 1

HCID 69056946HCID 69056946, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1-(1H-indole-2-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (0.500 g, 1.46 mmol) in CH2Cl2 (20 mL) was treated with TFA (8 mL). After 18 h at rt, the mixture was concentrated to give the title compound (520 mg, 99%). MS (ESI): mass calcd. for C16H17N3O, 243.14; m/z found, 244.4 [M+H]+. MS (ESI): mass calcd. for C14H16N3O, 243.43; m/z found, 244.3 [M+H]+. 1H NMR (MeOD): 7.68-7.63 (m, 1H), 7.48-7.43 (m, 1H), 7.28-7.21 (m, 1H), 7.11-7.05 (m, 1H), 7.05-7.00 (m, 1H), 4.44-3.76 (m, 5H), 2.85-2.74 (m, 3H), 2.67-2.08 (m, 2H).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-a963e7de246d4021ac8aed45d119dc66
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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