Diisopropylethylamine → HCID 86623403, compound

HRID 563141Notes

Reaction equation

HRID 563141 reaction equation
[CH2:1]([C:6]1[CH:38]=[CH:37][C:9]([CH2:10][N:11]([C:23](=[O:36])[CH:24]=[CH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[C@@H:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([OH:15])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:70]([N:72]1[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]1)=[O:71]>C(#N)C>[CH2:16]([C@H:12]([N:11]([CH2:10][C:9]1[CH:37]=[CH:38][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=1)[C:23](=[O:36])[CH:24]=[CH:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=1)[C:13]([N:75]1[CH2:76][CH2:77][N:72]([CH:70]=[O:71])[CH2:73][CH2:74]1)=[O:15])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 821911-PiperazinecarboxaldehydeHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67005271HCID 67005271, compound

Product 1

HCID 86623403HCID 86623403, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-{(4-pentyl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-(S)-3-phenyl-propionic acid (50 mg, 0.095 mmol) was dissolved in acetonitrile (1.0 ml), TBTU (37 mg, 0.115 mmol), DIPEA (37 mg, 0.29 mmol) and 1-formylpiperazine (12.23 mg, 0.105 mmol) was added and the mixture was stirred for 16 h at rt, filtered and directly purified by prep. HPLC to give 32 mg of N—[(S)-1-benzyl-2-(4-formyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=1.17 min; [M+H]+=620.50.

Workup

  1. filtrationfiltered
  2. customdirectly purified by prep

Sources & evidence

ORD record
ord-65172743815e49b7bd6b9b455b7deb15
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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