Cyclopropanecarbonyl chloride → 4-Chloro-2-(4-cyclopropanecarbonyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

HRID 1172508Notes

Reaction equation

HRID 1172508 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.C[O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:35])[C:14]2[O:20][C:19]3[C:21]([Cl:31])=[CH:22][C:23]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:33])(=[O:32])[C:15]=2[CH:34]=1)=[O:10]>ClCCl.N1C=CC=CC=1>[Cl:31][C:21]1[C:19]2[O:20][C:14]3[C:13]([CH3:35])=[CH:12][C:11]([C:9]([OH:10])=[O:8])=[CH:34][C:15]=3[S:16](=[O:32])(=[O:33])[CH2:17][C:18]=2[CH:24]=[C:23]([N:25]2[CH2:26][CH2:27][N:28]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:29][CH2:30]2)[CH:22]=1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284784-Chloro-2-(4-cyclopropanecarbonyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclopropyl carbonyl chloride (0.22 mL, 2.4 mmol) in dichloromethane (2 mL) was added to a suspension of Example 104k (0.35 g, 0.8 mmol) in pyridine (3 mL)/dichloromethane (1 mL) at 10° C. The reaction mixture was stirred for 45 min, concentrated, treated with chilled water and dilute HCl to pH 6. The precipitated solid was filtered and dried to obtain the title compound. Yield: 0.372 g, (91.5%); 1H NMR (DMSO-d6): δ 0.76 (m, 4H, 2CH2); 2.06 (m, 1H, CH); 2.68 (s, 3H, CH3); 3.24 (s, 2H, CH2); 3.32 (s, 2H, CH2); 3.64 (S, 2H, CH2); 3.84 (s, 2H, CH2); 5.15 (s, 2H, CH2); 7.12 (d, 1H, Ar); 7.2 (d, 1H, Ar); 8.1 (s, 1H, Ar); 8.2 (s, 1H, Ar); 8.38 (s, 1H, OH). MS: m/e (ES+) 532 (M+1).

Workup

  1. concentrationconcentrated
  2. additiontreated with chilled water and dilute HCl to pH 6
  3. filtrationThe precipitated solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-804ef2b204c441538344e11c80701567
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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