HCID 66791972, compound → HCID 66786176, compound

HRID 1096665Notes

Reaction equation

HRID 1096665 reaction equation
[CH2:1]([CH:8]([C:26]([N:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]2[N:38]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:37]3[CH:44]=[CH:45][CH:46]=[CH:47][C:36]=3[N:35]=2)[CH2:29]1)=[O:27])[C@H:9]([NH:18]C(=O)OC(C)(C)C)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[NH2:18][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:26]([N:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]2[N:38]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:37]3[CH:44]=[CH:45][CH:46]=[CH:47][C:36]=3[N:35]=2)[CH2:29]1)=[O:27]

Participants

3

Reactant 1

HCID 66791972HCID 66791972, compound

Product 1

HCID 66786176HCID 66786176, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (R)-3-benzyl-1-(4-chlorophenyl)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (131B) (0.25 mmole, 165 mg) in DCM (10 mL) was added TEA (2 mL). The reaction solution was stirred at rt for 1 hr and then concentrated in vacuo. The residue was purified by preparative LC/MS (25-30% CH3CN in H2O) to afford (R)-3-amino-2-benzyl-4-(4-chlorophenyl)-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one (240) (0.016 mmole, 9 mg, two-step yield: 6.4%). ESI-MS: m/z 560.4 (M+H)+. ESI-MS: m/z 560.4 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.49-1.74 (m, 1H) 1.82-1.95 (m, 1H) 2.01-2.33 (m, 3H) 2.50-2.95 (m, 3H) 2.95-3.09 (m, 2H) 3.11-3.23 (m, 1H) 3.24 (s, 3H) 3.44-3.59 (m, 2H) 3.62-3.95 (m, 2H) 4.62-4.86 (m, 4H) 5.88-6.10 (m, 2H) 7.18 (d, 0.1=6.25 Hz, 2H) 7.23-7.32 (m, 2H) 7.38 (d, J=2.40 Hz, 5H) 7.57-7.76 (m, 3H) 7.99-8.07 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (25-30% CH3CN in H2O)

Sources & evidence

ORD record
ord-ea445e0e2ef14773b0ba975c1476438e
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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