HCID 66791954, compound → HCID 56933313, compound

HRID 1096660Notes

Reaction equation

HRID 1096660 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([NH:39]C(=O)OC(C)(C)C)[CH2:16][C:17]([N:19]3[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]4[N:29]([CH2:30][CH2:31][CH2:32][O:33][CH3:34])[C:28]5[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=5[N:26]=4)[CH2:20]3)=[O:18])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>C(Cl)Cl>[NH2:39][C@H:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:9][CH:10]=1)[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]2[N:29]([CH2:30][CH2:31][CH2:32][O:33][CH3:34])[C:28]3[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=3[N:26]=2)[CH2:20]1)=[O:18]

Participants

3

Reactant 1

HCID 66791954HCID 66791954, compound

Product 1

HCID 56933313HCID 56933313, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (R)-1-(4-(4-hydroxypiperidin-1-yl)phenyl)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (0.325 mmole, 206 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 (10-15% CH3CN in H2O) to afford (R)-3-Amino-4-(4-(4-hydroxypiperidin-1-yl)phenyl)-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one (234) (0.024 mmole, 13 mg, two-step yield: 7.5%). ESI-MS: m/z 534.7 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.20-1.43 (m, 5H) 1.78-2.39 (m, 4H) 2.69-3.11 (m, 4H) 3.10-3.17 (m, 1H) 3.15-3.24 (m, 3H) 3.27 (s, 3H) 3.35-3.55 (m, 2H) 3.66-3.78 (m, 2H) 3.80-3.89 (m, 1H) 3.90-4.00 (m, 2 H) 4.37-4.46 (m, 1H) 4.48-4.58 (m, 1H) 4.59-4.67 (m, 2H) 4.67-4.76 (m, 1H) 7.30-7.35 (m, 1H) 7.38-7.46 (m, 3H) 7.55-7.67 (m, 2H) 7.73-7.82 (m, 1H) 7.83-7.93 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (10-15% CH3CN in H2O)

Sources & evidence

ORD record
ord-06cb04747fa54fe4a6a69ad24f817f69
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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