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

HRID 1927520Notes

Reaction equation

HRID 1927520 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[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]([CH3:3])[CH3:2])=[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 6363IsopropylamineHCID 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 1317285014-Chloro-2-(2-isopropylamino-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

Isopropyl amine (0.77 ml, 9 mmol) was added to a solution of Example 133 (0.4 g, 0.9 mmol) in DMF (10 mL). The reaction mixture was stirred at 80° C. for 2 h, 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. Yield: 0.172 g, (40%); 1H NMR (CDCl3): δ 1.22 (d, 6H, 2CH3), 2.7 (s, 3H, CH3), 2.87 (septet, 1H, CH), 3.38 (s, 2H, CH2), 3.92 (s, 3H, OCH3), 4.71 (s, 2H, CH2), 7.57 (s, 1H, Ar), 7.82 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar), 9.68 (s, 1H, NH); MS: m/e (ES+) 467 (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-de483803b7fd4be38c80c4b273843354
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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