HCID 68097900, compound → HCID 66786540, compound

HRID 1096659Notes

Reaction equation

HRID 1096659 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:52])[CH2:22][C@H:23]([NH:44]C(=O)OC(C)(C)C)[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:33](=[O:43])[CH2:32]3)=[CH:27][CH:26]=2)[CH2:16]1>C(Cl)Cl>[NH2:44][C@@H:23]([CH2:22][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@@H:15]([C:7]2[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH2:16]1)=[O:52])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:33](=[O:43])[CH2:32]2)=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 68097900HCID 68097900, compound

Product 1

HCID 66786540HCID 66786540, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (R)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxo-1-(4-(3-oxo-4-phenylpiperazin-1-yl)phenyl)butan-2-ylcarbamate (123A) (0.29 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 (45-55% CH3CN in H2O) to afford 4-(4-((R)-2-Amino-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutyl)phenyl)-1-phenylpiperazin-2-one (233) (0.11 mmole, 14 mg, two-step yield: 7.9%). ESI-MS: m/z 609.5 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.54-1.83 (m, 1H) 1.87-2.15 (m, 3H) 2.18-2.38 (m, 3H) 2.61-2.80 (m, 1H) 2.80-2.91 (m, 1H) 2.93-3.05 (m, 2H) 3.10-3.24 (m, 2H) 3.26 (s, 3H) 3.33-3.59 (m, 4H) 3.68 (t, J=5.43 Hz, 1H) 3.74-4.09 (m, 4H) 4.49-4.78 (m, 3H) 4.84 (br. s., 1H) 6.94-7.08 (m, 1H) 7.15-7.30 (m, 2H) 7.30-7.39 (m, 2H) 7.40-7.55 (m, 3H) 7.55-7.70 (m, 3H) 7.76-7.86 (m, 1H) 7.88-7.99 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (45-55% CH3CN in H2O)

Sources & evidence

ORD record
ord-2226b14e1a33487f93e2c92db65e955d
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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