Isobutyryl chloride → N-[4-(6-Chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzyl]-isobutyramide

HRID 220965

Reaction equation

HRID 220965 reaction equation
CCN(C(C)C)C(C)C.[C:10](Cl)(=[O:14])[CH:11]([CH3:13])[CH3:12].Cl.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([N:27]2[CH2:36][C:35]3[CH:34]=[N:33][N:32]([CH3:37])[C:31]=3[NH:30][C:29]3[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:28]2=3)=[O:26])=[CH:21][C:20]=1[F:43].C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+]>ClCCl>[Cl:42][C:39]1[CH:40]=[CH:41][C:28]2[N:27]([C:25]([C:22]3[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[C:20]([F:43])[CH:21]=3)=[O:26])[CH2:36][C:35]3[CH:34]=[N:33][N:32]([CH3:37])[C:31]=3[NH:30][C:29]=2[CH:38]=1

Participants

6

Reactant 4

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 164825Tartrazine2×HCID 136346648(4-Aminomethyl-3-fluoro-phenyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Hydrochloride

Product 1

HCID 135735995N-[4-(6-Chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzyl]-isobutyramideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (0.135 ml, 0.78 mmol) and isobutyryl chloride (0.029 ml, 0.27 mmol) were added to a solution of (4-aminomethyl-3-fluoro-phenyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride from Example E102.2 (110 mg, 0.26 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 1 h, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white powder identified as the title compound (85 mg, 71%).

Workup

  1. customat room temperature
  2. washwashed with saturated NaHCO3
  3. dry with materialbrine, dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  6. customto give a white powder

Sources & evidence

ORD record
ord-19cc54e88f3e4e4b9311635b7e3cb69e
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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