2-Methylbenzoic acid → HCID 11541305, compound

HRID 1695283Notes

Reaction equation

HRID 1695283 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[C:13]1([CH3:22])[C:14]([C:19](O)=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.[CH3:23][O:24][C:25]([C:27]1[CH:28]=[C:29]([CH3:51])[C:30]2[O:36][C:35]3[C:37]([Cl:47])=[CH:38][C:39]([N:41]4[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]4)=[CH:40][C:34]=3[CH2:33][S:32](=[O:49])(=[O:48])[C:31]=2[CH:50]=1)=[O:26]>CN(C=O)C>[CH3:23][O:24][C:25]([C:27]1[CH:28]=[C:29]([CH3:51])[C:30]2[O:36][C:35]3[C:37]([Cl:47])=[CH:38][C:39]([N:41]4[CH2:42][CH2:43][N:44]([C:19](=[O:20])[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=5[CH3:22])[CH2:45][CH2:46]4)=[CH:40][C:34]=3[CH2:33][S:32](=[O:48])(=[O:49])[C:31]=2[CH:50]=1)=[O:26]

Participants

5

Reactant 3

HCID 83732-Methylbenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 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 11541305HCID 11541305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
22 °C

Procedure

Carbonyl diimidazole (0.074 g 0.55 mmol) was added to a solution of 2-toluic acid (0.111 g, 0.67 mmol) in DMF (3 mL) and stirred at 22° C. for 1 h. To this, a solution of 4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (free base of example 16, 0.2 g, 0.45 mmol) in DMF (2 mL) was added and stirred at 22° C. for 1 h. Solvent was removed and ice water (5 mL) was added. The solid separated was filtered, washed with water. The crude product obtained was purified by column chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound. Yield: 0.093 g (53%); mp: 201-204° C.; 1H NMR (DMSO-d6, 500 MHz): δ 2.23 (s, 3H, CH3), 2.64 (s, 3H, CH3), 3.15 (s, 2H, CH2), 3.28 (s, 2H, CH2), 3.34 (s, 2H, CH2), 3.39 (s, 2H, CH2), 3.87 (s, 3H, OCH3), 5.16 (s, 2H, CH2), 7.12 (s, 1H, Ar), 7.16 (s, 1H, Ar), 7.20 (m, 4H, Ar), 8.11 (s, 1H, Ar), 8.16 (s, 1H, Ar); MS: m/e (ES+) 555 (M+1).

Workup

  1. stirringstirred at 22° C. for 1 h
  2. customSolvent was removed
  3. additionice water (5 mL) was added
  4. customThe solid separated
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe crude product obtained
  8. customwas purified by column chromatography (silica gel, ethyl acetate/pet ether)

Sources & evidence

ORD record
ord-e3954c609bff48da8fbe24ed2ac2191e
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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