Diisopropylethylamine → HCID 67005528, compound

HRID 563146Notes

Reaction equation

HRID 563146 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.CCN(C(C)C)C(C)C.[CH2:33]([N:40]1[CH2:45][CH2:44][N:43]([C:46](=[O:68])[C@@H:47]([NH:55][CH2:56][C:57]2[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:59][CH:58]=2)[CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:48]([C@H:47]([N:55]([CH2:56][C:57]1[CH:58]=[CH:59][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:61][CH:62]=1)[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:46]([N:43]1[CH2:42][CH2:41][N:40]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:45][CH2:44]1)=[O:68])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 59808329HCID 59808329, compound

Product 1

HCID 67005528HCID 67005528, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere, trans-4-(trifluoromethyl)cinnamic acid (28 mg, 0.13 mmol) was dissolved in DCM (0.5 mL) followed by the addition of 1-chloro-N,N,2-trimethylpropenylamine (19.4 mg, 0.145 mmol). The mixture was stirred at rt for 30 min followed by the addition of DIPEA (34 mg, 0.26 mmol) and 1-(4-benzyl-piperazin-1-yl)-2-(4-butoxy-benzylamino)-(S)-3-phenyl-propan-1-one (63 mg, 0.13 mmol). Stirring was continued for 30 min. The mixture was concentrated in vacuo and the residue was directly purified by prep. HPLC to give 51 mg (57%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-butoxy-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=1.02 min; [M+H]+=684.49.

Workup

  1. stirringStirring
  2. waitwas continued for 30 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was directly purified by prep

Sources & evidence

ORD record
ord-5e836015fad04c1d880496785d57886d
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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