HCID 68098439, compound → HCID 66784773, compound

HRID 1096658Notes

Reaction equation

HRID 1096658 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@@H:17]([NH:41]C(=O)OC(C)(C)C)[CH2:18][C:19]([N:21]3[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]4[N:31]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:30]5[CH:37]=[CH:38][CH:39]=[CH:40][C:29]=5[N:28]=4)[CH2:22]3)=[O:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@@H:17]([NH2:41])[CH2:18][C:19]([N:21]3[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]4[N:31]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:30]5[CH:37]=[CH:38][CH:39]=[CH:40][C:29]=5[N:28]=4)[CH2:22]3)=[O:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 68098439HCID 68098439, compound

Product 1

HCID 66784773HCID 66784773, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (R)-1-(4-(4-acetylpiperazin-1-yl)phenyl)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (122A) (0.29 mmole, 202 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 (10-25% CH3CN in H2O) to afford (R)-4-(4-(4-Acetylpiperazin-1-yl)phenyl)-3-amino-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one (232) (0.0018 mmole, 1.5 mg, two-step yield: 0.9%). ESI-MS: m/z 561.5 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.90-2.12 (m, 3H) 2.15 (s, 3H) 2.18-2.37 (m, 3H) 2.58-3.04 (m, 2H) 3.11-3.24 (m, 6H) 3.27 (s, 3H) 3.39-3.60 (m, 4H) 3.65-3.76 (m, 4H) 3.79 (dd, J=9.13, 4.58 Hz, 1H) 3.94 (d, J=14.21Hz, 1H) 4.14 (d, J=15.03 Hz, 1H) 4.42-4.60 (m, 1H) 4.64 (t, J=6.92 Hz, 1H) 4.72 (d, J=14.15 Hz, 1H) 6.96-7.05 (m, 2H) 7.14-7.24 (m, 2H) 7.56-7.66 (m, 2H) 7.75-7.82 (m, 1H) 7.86-7.93 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (10-25% CH3CN in H2O)

Sources & evidence

ORD record
ord-f3c1c6a7daba4085b3dc3d4630732967
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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