Cyclopropylamine → 4-Chloro-2-(2-cyclopropylamino-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927517Notes

Reaction equation

HRID 1927517 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:32])[C:12]2[O:18][C:17]3[C:19]([Cl:28])=[CH:20][C:21]([NH:23][C:24](=[O:27])[CH2:25]Cl)=[CH:22][C:16]=3[CH2:15][S:14](=[O:30])(=[O:29])[C:13]=2[CH:31]=1)=[O:8]>CN(C=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:32])[C:12]2[O:18][C:17]3[C:19]([Cl:28])=[CH:20][C:21]([NH:23][C:24](=[O:27])[CH2:25][NH:4][CH:1]4[CH2:3][CH2:2]4)=[CH:22][C:16]=3[CH2:15][S:14](=[O:30])(=[O:29])[C:13]=2[CH:31]=1)=[O:8]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 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 1317284984-Chloro-2-(2-cyclopropylamino-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropyl amine (0.285 ml, 4.067 mmol) was added to a solution of Example 133 (0.6 g, 1.35 mmol) in DMF (15 mL) and the reaction mixture was stirred at 80° C. for 2 h. It was concentrated, treated with water and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 2% methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.58 g (92%); 1H NMR (CDCl3): δ 0.6 (s, 4H, 2CH2), 2.4 (m, 1H, CH), 2.67 (s, 3H, CH3), 3.6 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 4.7 (s, 2H, CH2), 7.6 (s, 1H, Ar), 7.65 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar), 9.35 (bs, 1H, NH); MS: m/e (ES+) 465 (M+1).

Workup

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

Sources & evidence

ORD record
ord-edbfc17aab2843edbf48ed0b1a8cf857
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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