Methanol → 4-Chloro-2-[(2-methoxy-acetyl)-(2-pyrrolidin-1-yl-ethyl)-amino]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927478Notes

Reaction equation

HRID 1927478 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:37])[C:14]2[O:20][C:19]3[C:21]([Cl:33])=[CH:22][C:23]([NH:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:35])(=[O:34])[C:15]=2[CH:36]=1)=[O:10].CO>O>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:37])[C:14]2[O:20][C:19]3[C:21]([Cl:33])=[CH:22][C:23]([N:25]([C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:34])(=[O:35])[C:15]=2[CH:36]=1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 96623Methoxyacetyl chlorideHCID 1317284574-Chloro-6-methyl-10,10-dioxo-2-(2-pyrrolidin-1-yl-ethylamino)-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284614-Chloro-2-[(2-methoxy-acetyl)-(2-pyrrolidin-1-yl-ethyl)-amino]-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 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Methoxy-acetyl chloride (0.6 mL, 6.4 mmol) was added to a solution of Example 72k (0.3 g, 0.64 mmol) with stirring. The temperature was raised to 80° C. and stirring continued for 2 h. The reaction mixture was treated with methanol (1 mL), water and extracted with chloroform. The organic layer was washed with water, brine, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.260 g (75.14%); 1H NMR (DMSO-d6): δ 0.71 (bs, 4H, 2CH2), 2.60 (bs, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.20 (s, 3H, OCH3), 3.70 (s, 3H, CH3), 3.80 (bs, 4H, 2CH2), 4.00 (s, 3H, OCH3), 5.40 (s, 2H, CH2), 7.65 (s, 1H, Ar), 7.80 (s, 1H, Ar), 8.19 (s, 1H, Ar). 8.22 (s, 1H, Ar); MS: m/e (CI+) 533 (M+1).

Workup

  1. stirringstirring
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. custompurified

Sources & evidence

ORD record
ord-ee77741817984e65ad954333725171d4
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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