Dimethylformamide → 4-(2-Piperidinon-1-yl)piperidin-1-yl-2-phenyl-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2245003Notes

Reaction equation

HRID 2245003 reaction equation
[C:1]([N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)CC(O)=O)([O:3]C(C)(C)C)=O.[ClH:19].[N:20]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=[O:26].C([N:35]([CH2:38][CH3:39])CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2N=N1.C[N:68]([CH:70]=[O:71])C>CCOC(C)=O.O>[N:20]1([CH:27]2[CH2:32][CH2:31][N:30]([C:38]([C:39]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:50]=3)([NH:35][C:1]([NH:8][C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)=[O:3])[C:70]([NH2:68])=[O:71])[CH2:29][CH2:28]2)[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=[O:26]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycineHCID 23138456[1,4']Bipiperidinyl-2-one hydrochloride

Product 1

HCID 695728764-(2-Piperidinon-1-yl)piperidin-1-yl-2-phenyl-2-(4-chlorophenylaminocarbonylamino)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of(D) N-BOC phenylglycine (32 mg, 0.13 mmol), 4-(2-piperidinon-1-yl)piperidine hydrochloride (22 mg, 0.10 mmol) and triethylamine (0.070 mL, 0.50 mmol) in DMF (1.0 mL), BOP (66 mg, 0.15 mmol) was added. The mixture was stirred at room temperature for 20 min. Water and EtOAc were added. The EtOAc phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo to give the amide (51 mg). MS 416.5 (M+H).

Workup

  1. customThe EtOAc phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0a4a27eeb07448abfc79007e1225c0a
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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