HCID 66791512, compound → HCID 66784278, compound

HRID 1096639Notes

Reaction equation

HRID 1096639 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:39])[CH2:18][C@H:19]([NH:31]C(=O)OC(C)(C)C)[CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=4)[CH2:12]3)[N:8]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:7]=2[CH:45]=1>C(Cl)Cl>[NH2:31][C@H:19]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[CH2:18][C:17]([N:13]1[CH2:14][CH2:15][CH2:16][CH:11]([C:9]2[N:8]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:7]3[CH:45]=[C:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=3[N:10]=2)[CH2:12]1)=[O:39]

Participants

3

Reactant 1

HCID 66791512HCID 66791512, compound

Product 1

HCID 66784278HCID 66784278, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2R)-4-(3-(6-(hydrox ymethyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(naphthalen-2-yl)-4-oxobutan-2-ylcarbamate (45A) (0.20 mmol, 120 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 (5-45% CH3CN in H2O) to afford (3R)-3-amino-1-(3-(6-(hydroxymethyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one (113) (0.016 mmol, 8 mg, two-step yield: 13.3%). ESI-MS: m/z 515.5 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.56-1.70 (m, 1H) 1.77-2.09 (m, 2H) 1.85-1.86 (m, 3H) 2.12-2.34 (m, 3H) 2.63-3.02 (m, 4H) 3.03-3.11 (m, 2H) 3.13 (d, J=7.26 Hz, 2H) 3.15-3.27 (m, 3H) 3.29 (s, 1H) 3.36-3.51 (m, 3H) 3.67-4.29 (m, 4H) 4.50-4.72 (m, 1H) 7.39-7.44 (m, 2H) 7.49 (ddd, J=9.32, 6.06, 2.81Hz, 3H) 7.56 (d, 0.7=8.65 Hz, 1H) 7.69-7.74 (m, 1H) 7.79-7.94 (m, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (5-45% CH3CN in H2O)

Sources & evidence

ORD record
ord-1aebf9db21d64cf59a8ad663f28dbdc9
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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