Acetyl chloride → HCID 11227399, compound

HRID 2099797Notes

Reaction equation

HRID 2099797 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH:21]([C:36]3[N:37]([CH2:41][C:42]4[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[CH:43]=4)[CH:38]=[CH:39][N:40]=3)[CH2:22][C:23]3[CH:31]=[C:30]([CH3:32])[C:29]4[C:25](=[CH:26][N:27](COC)[N:28]=4)[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(Cl)(=O)C>CO>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C@@H:21]([C:36]3[N:37]([CH2:41][C:42]4[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[CH:43]=4)[CH:38]=[CH:39][N:40]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 69065568HCID 69065568, compound

Product 1

HCID 11227399HCID 11227399, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(1-(3,5-difluorobenzyl)-1H-imidazol-2-yl)-2-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (72.0 mg, 0.108 mmol) and acetyl chloride (0.18 mL) were combined in methanol (2.0 mL) and heated at reflux for 1 h. After cooling to room temperature, the solvents were removed in vacuo. Column chromatography afforded 47 mg (70%). 1H-NMR (CD3OD, 500 MHz) δ 1.38-2.05 (m, 3H), 2.45 (s, 3H), 2.70-3.05 (m, 3H), 3.24 (dd, J=7.3, 7.3, 1H), 3.45-3.55 (m, 1H), 4.05-4.40 (m, 2H), 5.05-5.45 (m, 2H), 5.50 (s, 1H), 5.95 (bs, 1H), 6.34-6.90 (m, 4H), 7.17 (s, 1H), 7.25 (m, 2H), 7.34 (d, J=8.2, 1H), 7.45-7.75 (m, 3H), 7.90 (s, 1H). Mass spec.: 623.3 (MH)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe solvents were removed in vacuo
  4. customColumn chromatography afforded 47 mg (70%)

Sources & evidence

ORD record
ord-7d3401f2234c42f39167ef71992175eb
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…