Phenyl chloroformate → HCID 15603610, compound

HRID 1486779Notes

Reaction equation

HRID 1486779 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]3[C:26]4[N:25]=[C:24]([CH:27]([CH3:29])[CH3:28])[NH:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)=[O:17])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.Cl[C:40]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:41]>ClCCl>[C:43]1([O:42][C:40]([N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][N:8]3[CH2:9][CH2:10][CH:11]([CH2:14][NH:15][C:16]([C:18]4[C:26]5[N:25]=[C:24]([CH:27]([CH3:29])[CH3:28])[NH:23][C:22]=5[CH:21]=[CH:20][CH:19]=4)=[O:17])[CH2:12][CH2:13]3)[CH2:5][CH2:6]2)=[O:41])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 66810992HCID 66810992, compound

Product 1

HCID 15603610HCID 15603610, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-isopropyl-1H-benzoimidazole-4-carboxylic acid (1-piperidin-4-ylmethylpiperidin-4-ylmethyl)amide (0.22 g, 0.55 mmol) and N,N-diisopropylethylamine (0.19 mL) in dichloromethane (5.0 mL) was added phenyl chloroformate (70 μL). The mixture was stirred at room temperature for 10 min, then concentrated in vacuo and purified via preparative reverse phase HPLC to afford the bis trifluoroacetate salt of the title compound as a white solid (98.4 mg, 0.13 mmol, 24%). (m/z): [M+H]+ calcd for C30H39N5O3 518.32. found 518.6. 1H NMR (300 MHz, MeOD-d3): δ (ppm) 1.14-1.28 (m, 2H), 1.39-1.53 (m, 6H), 1.52-1.62 (m, 2H), 1.70-1.78 (m, 2H), 1.92-2.06 (m, 4H), 2.82-2.97 (m, 6H), 3.32-3.38 (m, 2H), 3.43-3.50 (m, 1H), 3.52-3.69 (m, 2H), 4.04-4.12 (m, 1H), 4.18-4.26 (m, 1H), 6.91-6.98 (m, 1H), 7.08-7.13 (m, 1H), 7.21-7.28 (m, 1H), 7.45-7.50 (m, 1H), 7.73-7.77 (m, 1H), 7.81-7.87 (m, 1H), 9.02-9.32 (brs, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-4c2b83c0d4d448d8a30b398ce32b85e8
Source dataset
uspto-grants-2016_08
Patent number
US09428489B2

Reaction notes

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