Isobutyryl chloride → HCID 46841136, compound

HRID 1846320Notes

Reaction equation

HRID 1846320 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]2[C:25]2[CH:30]=[C:29]([CH3:31])[C:28]([O:32][CH2:33][CH2:34][OH:35])=[C:27]([CH3:36])[CH:26]=2)=[CH:10][CH:9]=1>C(Cl)Cl>[OH:35][CH2:34][CH2:33][O:32][C:28]1[C:27]([CH3:36])=[CH:26][C:25]([C:15]2[N:14]([C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:9][CH:10]=3)[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:30][C:29]=1[CH3:31]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 46841271HCID 46841271, compound

Product 1

HCID 46841136HCID 46841136, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.07 mL, 0.50 mmol) and isobutyryl chloride (0.25 mmol) were added to a solution of 3-(4-aminophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.100 g, 0.25 mmol) in CH2Cl2 (5 mL), stirred at room temperature for 2 hours, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 2% to 10% MeOH in CH2Cl2, afforded the title compound as a white solid in 78% yield. 1H-NMR (300 MHz, DMSO-d6): δ 9.90 (s, 1H), 8.17 (dd, J=6.8, 1.2 Hz, 1H), 7.85-7.91 (m, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.53-7.65 (m, 3H), 7.20 (d, J=8.9 Hz, 2H), 7.04 (s, 2H), 4.83 (t, J=5.4 Hz, 1H), 3.61-3.72 (m, 4H), 2.56-2.63 (m, 1H), 2.10 (s, 6H), 1.08 (d, J=6.9 Hz, 6H). MS (APCI) m/z: 472 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 2% to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-d7e87a0d84c341f4987178469af06014
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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