1-Chloro-N,N-2-trimethylpropenylamine → HCID 67005722, compound

HRID 563148Notes

Reaction equation

HRID 563148 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1.ClC(N(C)C)=C(C)C.[CH2:24]([N:31]1[CH2:36][CH2:35][N:34]([C:37](=[O:57])[C@@H:38]([NH:46][CH2:47][C:48]2[CH:49]=[C:50]3[C:54](=[CH:55][CH:56]=2)[NH:53][CH:52]=[CH:51]3)[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH2:39]([C@H:38]([N:46]([CH2:47][C:48]1[CH:49]=[C:50]2[C:54](=[CH:55][CH:56]=1)[NH:53][CH:52]=[CH:51]2)[C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=1)[C:37]([N:34]1[CH2:33][CH2:32][N:31]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:36][CH2:35]1)=[O:57])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 59808274HCID 59808274, compound

Product 1

HCID 67005722HCID 67005722, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere, trans-4-(trifluoromethyl)cinnamic acid (34 mg, 0.156 mmol) was dissolved in DCM (3 mL) and 1-chloro-N,N,2-trimethylpropenylamine (24 mg, 0.182 mmol) was added at rt. The reaction mixture was stirred for 30 min followed by the addition of 1-(4-benzyl-piperazin-1-yl)-2-[(1H-indol-5-ylmethyl)-amino]-(S)-3-phenyl-propan-1-one (59 mg, 0.13 mmol). Stirring was continued at rt for 3 h. The solvents were evaporated under reduced pressure and the residue was directly purified by prep. HPLC to give 33 mg (39%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(1H-indol-5-ylmethyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=0.96 min; [M+H]+=651.24.

Workup

  1. stirringStirring
  2. waitwas continued at rt for 3 h
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue was directly purified by prep

Sources & evidence

ORD record
ord-3cb6037354514f5994f978de59fcd6c9
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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