Acetyl chloride → HCID 68676702, compound

HRID 1992160Notes

Reaction equation

HRID 1992160 reaction equation
[NH2:1][C:2]([CH2:40][CH3:41])([CH2:38][CH3:39])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)([CH2:11][CH2:12][N:13]2[CH:18]3[CH2:19][CH2:20][CH:14]2[CH2:15][CH:16]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH3:30])[CH2:17]3)[CH2:7][CH2:6]1)=[O:4].[C:42](Cl)(=[O:44])[CH3:43].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:38]([C:2]([NH:1][C:42](=[O:44])[CH3:43])([C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)([CH2:11][CH2:12][N:13]2[CH:18]3[CH2:19][CH2:20][CH:14]2[CH2:15][CH:16]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH3:30])[CH2:17]3)[CH2:7][CH2:6]1)=[O:4])[CH2:40][CH3:41])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58727859HCID 58727859, compound

Product 1

HCID 68676702HCID 68676702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-Amino-2-ethyl-1-(4-(3-fluoro-phenyl)-4-{2-[3-(2-methyl-benzoimidazol-1-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-ethyl}-piperidin-1-yl)-butan-1-one (0.100 g, 0.178 mmol), acetyl chloride (0.014 g, 0.178 mmol) and DIEA (0.069 g, 0.534 mmol) were stirred at room temperature in DCM (3 ml) for 2 hours. Solvent was removed and compound was purified by RP-HPLC to yield 0.072 g (67%). 1H NMR (400 MHz, CDCl3) 7.67 (m, 1H), 7.40-7.29 (m, 2H), 7.18 (m, 2H), 7.09 (m, 1H), 6.99 (m, 2H), 4.60 (m, 1H) 4.04 (br, 2H), 3.32-3.23 (m, 4H), 2.74 (m, 2H), 2.57 (s, 3H), 2.36 (m, 2H), 2.20 (m, 2H), 2.01 (s, 3H), 1.92 (m, 6H), 1.82-1.63 9 (m, 10H), 0.78 (br, 5H). ES-LCMS m/z 602 (M+1).

Workup

  1. customSolvent was removed
  2. customcompound was purified by RP-HPLC
  3. customto yield 0.072 g (67%)

Sources & evidence

ORD record
ord-d20ed0e13b0246229af148e5907b1dc8
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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