Isobutyryl chloride → HCID 178432330, compound

HRID 220996Notes

Reaction equation

HRID 220996 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[N:23]=[C:22]([CH3:27])[NH:21][C:20]=3[C:19]3[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:18]2=3)=[O:16])=[CH:11][C:10]=1[CH3:33].CCN(C(C)C)C(C)C>ClCCl>[Cl:32][C:29]1[CH:30]=[CH:31][C:18]2[N:17]([C:15]([C:12]3[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[C:10]([CH3:33])[CH:11]=3)=[O:16])[CH2:26][CH2:25][C:24]3[N:23]=[C:22]([CH3:27])[NH:21][C:20]=3[C:19]=2[CH:28]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 178432329HCID 178432329, compound

Product 1

HCID 178432330HCID 178432330, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (0.07 ml, 0.07 mmol) was added to a solution of (4-aminomethyl-3-methyl-phenyl)-(9-chloro-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-methanone from Example E125.3 (24 mg, 0.07 mmol) in dichloromethane (3 ml) and DIEA (0.10 ml, 0.57 mmol) at 0° C. The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane to 10% methanol:90% di-chloromethane) to give a colourless oil identified as the title compound 24 mg, 85%).

Workup

  1. customat 0° C
  2. customsolvents were removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane to 10% methanol:90% di-chloromethane)
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-09447532d6e44bc8b5fd4472c67f285b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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