HCID 66791724, compound → HCID 66785192, compound

HRID 1096593Notes

Reaction equation

HRID 1096593 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:40])[CH2:17][C@H:18]([NH:32]C(=O)OC(C)(C)C)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:11]1>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:40])[CH2:17][C@H:18]([NH2:32])[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH2:11]1

Participants

3

Reactant 1

HCID 66791724HCID 66791724, compound

Product 1

HCID 66785192HCID 66785192, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (R)-4-((R)-3-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(biphenyl-4-yl)-4-oxobutan-2-ylcarbamate (5C) (0.22 mmol, 120 mg) in DCM (5 mL) was added TEA (1 mL). The reaction solution was stirred at rt for 1 h and then concentrated in vacuo. The residue was purified by preparative LC/MS (20-50% CH3CN in H2O) to afford the title compound (R)-1-((R)-3-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-3-amino-4-(biphenyl-4-yl)butan-1-one (71) (0.14 mmol, 63 mg, two-step yield: 63.6%). ESI-MS: m/z 439.4 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.56-1.75 (m, 1H) 1.92 (ddd, J=13.77, 7.29, 3.51Hz, 1H) 2.06 (dd, J=13.01, 3.66 Hz, 1H) 2.38 (dd, J=9.09, 3.73 Hz, 1H) 2.69-2.89 (m, 2H) 3.00-3.16 (m, 2H) 3.16-3.26 (m, 1H) 3.39-3.49 (m, 1H) 3.88 (ddd, J=10.80, 7.33, 3.79 Hz, 1H) 4.32 (d, J=9.54 Hz, 1H) 4.64 (d, J=13.14 Hz, 1H) 4.83 (dd, J=12.92, 3.44 Hz, 1H) 7.29-7.46 (m, 5H) 7.54-7.66 (m, 6H) 7.77 (dd, J=6.16, 3.13 Hz, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (20-50% CH3CN in H2O)

Sources & evidence

ORD record
ord-ad2c263a431d44d9834128b1181d677d
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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