HCID 66786129, compound → HCID 56933183, compound

HRID 1096638Notes

Reaction equation

HRID 1096638 reaction equation
C(OC([NH:8][C@H:9]([CH2:37][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=1)[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[N:23]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:22]3[C:29]([C:33]([O:35][CH3:36])=[O:34])=[CH:30][CH:31]=[CH:32][C:21]=3[N:20]=2)[CH2:14]1)=[O:12])=O)(C)(C)C>C(Cl)Cl>[NH2:8][C@H:9]([CH2:37][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=1)[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[N:23]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:22]3[C:29]([C:33]([O:35][CH3:36])=[O:34])=[CH:30][CH:31]=[CH:32][C:21]=3[N:20]=2)[CH2:14]1)=[O:12]

Participants

3

Reactant 1

HCID 66786129HCID 66786129, compound

Product 1

HCID 56933183HCID 56933183, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(1-((R)-3-(tert-butoxycarbonylamino)-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-1-(3-methoxypropyl)-1H-benzo[d]imidazole-7-carboxylate (440) (0.04 mmol, 25 mg) in DCM (5 mL) was added TEA (1 mL). The reaction solution was stirred at rt for 1 hr and then concentrated in vacuo. The residue was purified by preparative LC/MS (20-50% a CH3CN in H2O) to afford methyl 2-(1-((R)-3-amino-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-1-(3-methoxypropyl)-1H-benzo[d]imidazole-7-carboxylate (112) (0.018 mmol, 10 mg, yield: 45.0%). ESI-MS: 543.5 m/z (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.52-1.74 (m, 2H) 1.85-2.11 (m, 4H) 2.15-2.32 (m, 2H) 2.65 (s, 2H) 2.69-2.89 (m, 4H) 2.90-3.09 (m, 4H) 3.23 (s, 1H) 3.35 (t, J=5.53 Hz, 1H) 3.40-3.50 (m, 1H) 3.89 (d, J=13.83 Hz, 1H) 4.34-4.44 (m, 2H) 4.57 (dd, 2H) 4.66 (d, 0.1=13.07 Hz, 2H) 7.43 (t, J=8.12 Hz, 1H) 7.47-7.53 (m, 2H) 7.56 (t, J=8.72 Hz, 1H) 7.76-7.93 (m, 4H) 7.93-7.98 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-10ec09178f924aac980f298473658e19
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

Loading…