Cyclobutylamine → HCID 131728503, compound

HRID 1927522Notes

Reaction equation

HRID 1927522 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:33])[C:13]2[O:19][C:18]3[C:20]([Cl:29])=[CH:21][C:22]([NH:24][C:25](=[O:28])[CH2:26]Cl)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:30])[C:14]=2[CH:32]=1)=[O:9]>CN(C=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:33])[C:13]2[O:19][C:18]3[C:20]([Cl:29])=[CH:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][NH:5][CH:1]4[CH2:4][CH2:3][CH2:2]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:30])[C:14]=2[CH:32]=1)=[O:9]

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728503HCID 131728503, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cyclobutylamine (0.192 g, 2.7 mmol) was added to a solution of Example 133 (0.600 g, 1.3 mmol) in DMF (1 mL). The reaction mixture was stirred at 120° C. for 4 h, concentrated, treated with water and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 3-4% methanol/chloroform) to obtain the title compound. Yield: 0.450 g, (66.6%); 1H NMR (CDCl3-d6): δ 1.80 (m, 6H, 3CH2), 1.94 (t, 3H, CH3), 2.2 (t, 1H, CH), 2.9 (s, 3H, CH3), 3.3 (s, 2H, CH2), 3.9 (s, 3H, CH3), 4.7 (s, 2H, CH2), 7.5 (s, 1H, Ar), 7.8 (s, 1H, Ar). 8.4 (s, 1H, Ar), 9.5 (s, 1H, Ar); MS: m/e (ES+) 423 (M+1).

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. custompurified

Sources & evidence

ORD record
ord-8932857b4f714077ab3f3a9a1be75dd3
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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