Acetic Anhydride → (2E)-3-(1-acetamido-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide

HRID 339132Notes

Reaction equation

HRID 339132 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[CH:12]/[C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:17]([F:20])([F:19])[F:18])=[O:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.CN1CC[O:35][CH2:34][CH2:33]1.C(OC(=O)C)(=O)C>ClCCl>[C:34]([NH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[CH:12]/[C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)[C:17]([F:18])([F:19])[F:20])=[O:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)(=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79724-MethylmorpholineHCID 86653078(2E)-3-(1-Amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}acrylamide

Product 1

HCID 86653079(2E)-3-(1-acetamido-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamideYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg of (2E)-3-(1-amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)-phenyl]ethyl}acrylamide were dissolved in 5 ml of dichloromethane, admixed with 71 mg of N-methylmorpholine and 36 mg of acetic anhydride, and stirred at room temperature overnight. The reaction mixture was concentrated on a rotary evaporator to obtain 165 mg of (2E)-3-(1-acetamido-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide (100%).

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-4d5e0a0ab1b64588b862b0f9d1634423
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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