HCID 66786057, compound → HCID 56933182, compound

HRID 1096634Notes

Reaction equation

HRID 1096634 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[CH:29]=[C:30]([C:33]([O:35][CH3:36])=[O:34])[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[CH:29]=[C:30]([C:33]([O:35][CH3:36])=[O:34])[CH:31]=[CH:32][C:21]=3[N:20]=2)[CH2:14]1)=[O:12]

Participants

3

Reactant 1

HCID 66786057HCID 66786057, compound

Product 1

HCID 56933182HCID 56933182, compoundYield 22.7%

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-6-carboxylate (43D) (0.22 mmol, 140 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 (20-50% CH3CN in H2O) to afford methyl 2-(14(R)-3-amino-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-1-(3-methoxypropyl)-1H-benzo[d]imidazole-6-carboxylate (111) (0.05 mmol, 26 mg, yield: 22.7%). ESI-MS: m/z 543.5 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-2.12 (m, 6H) 2.70 (d, J=6.51Hz, 3H) 2.87-3.06 (m, 2H) 3.06-3.19 (m, 4H) 3.19-3.25 (m, 2H) 3.30 (t, J=5.62 Hz, 1H) 3.27-3.32 (m, 1H) 3.74-3.85 (m, 2H) 3.89 (d, J=6.88 Hz, 3H) 3.96 (s, 1H) 4.18-4.60 (m, 3H) 7.44 (dd, J=9.03, 6.13 Hz, 1H) 7.48-7.56 (m, 2H) 7.63-7.72 (m, 1H) 7.80 (d, J=7.39 Hz, 1H) 7.84 (dd, J=8.91, 2.08 Hz, 2H) 7.87-7.95 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-cb6e30de28e84de09961c1b5332cb88f
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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