Water → HCID 18617788, compound

HRID 1264313Notes

Reaction equation

HRID 1264313 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:33])[NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[C:25]3[C:31]#[N:32])=[CH:14][CH:13]=1)([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[NH2:7][CH2:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[C:25]3[C:31]#[N:32])=[O:33])=[CH:16][CH:17]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 70026887HCID 70026887, compound

Product 1

HCID 18617788HCID 18617788, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-[4-[2-(3-cyano-1H-indol-5-yl)-ethylcarbamoyl]-phenyl]-2-methyl-propyl)-carbamic acid tert-butyl ester (1.16 g, 2.5 mmol) (prepared using the procedure of reference example 1w) in CH2Cl2 (8 ml) was added TFA (1.6 ml) and the reaction stirred 2 hrs. Water (50 μL) was add-ed and the reaction concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 10% 7M NH3 in CH3OH/CH2Cl2) to give 808 mg of product. MS (ion spray) m/z 361 (M+H)+.

Workup

  1. concentrationthe reaction concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (eluting with 10% 7M NH3 in CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ee40c02ea0e1427494b2508276b4c1db
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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