HCID 11648633, compound → HCID 11582937, compound

HRID 1695291Notes

Reaction equation

HRID 1695291 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:32])[C:8]2[O:14][C:13]3[C:15]([Cl:28])=[CH:16][C:17]([N:19]4[CH2:24][CH2:23][N:22]([C:25](=O)[CH3:26])[CH2:21][CH2:20]4)=[CH:18][C:12]=3[CH2:11][S:10](=[O:30])(=[O:29])[C:9]=2[CH:31]=1)=O>C1COCC1>[Cl:28][C:15]1[C:13]2[O:14][C:8]3[C:7]([CH3:32])=[CH:6][C:5]([CH2:3][OH:2])=[CH:31][C:9]=3[S:10](=[O:29])(=[O:30])[CH2:11][C:12]=2[CH:18]=[C:17]([N:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH2:24]2)[CH:16]=1

Participants

3

Reactant 1

HCID 11648633HCID 11648633, compound2×

Product 1

HCID 11582937HCID 11582937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Boranedimethylsulphide complex (0.85 mL, 8.7 mmol) was added at 10° C. to a stirred solution of 2-(4-acetyl-piperazin-1-yl)-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid (0.8 g, 1.7 mmol) [obtained by hydrolysis of compound of Example 21] in dry THF (70 mL) under nitrogen atmosphere. The reaction mixture was stirred at 60° C. for 2 h. Reaction mixture was cooled and quenched with methanol and the solvent was removed. Solid was suspended in ethylacetate (100 mL) and washed with water, brine and dried over sodium sulphate. The crude product obtained was purified by column chromatography (silica gel, 2% methanol-chloroform) to obtain the title compound. Yield: 0.5 g (67.74%); mp: 230-32° C.; 1H NMR (DMSO-d6, 300 MHz): δ 1.88 (t, 3H, CH3), 2.57 (s, 3H, CH3), 2.86 (t, 2H, CH2), 2.88-2.91 (m, 4H, 2CH2), 3.31-3.41 (m, 4H, 2CH2), 4.45 (d, 2H, CH2), 5.04 (s, 2H, CH2), 5.37 (t, 1H, OH), 7.07 (s, 1H, Ar), 7.13 (s, 1H, Ar), 7.43 (s, 1H, Ar), 7.58 (s, 1H, Ar); MS: m/e (ES+) 437 (M+1).

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. customquenched with methanol
  4. customthe solvent was removed
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulphate
  7. customThe crude product obtained
  8. customwas purified by column chromatography (silica gel, 2% methanol-chloroform)

Sources & evidence

ORD record
ord-fa1afdaf968e4e7ea6f6c0a920dbfdba
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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