Benzyl Alcohol → HCID 11699783, compound

HRID 1173368Notes

Reaction equation

HRID 1173368 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:21][O:22][C:23]([C:25]1[CH:26]=[C:27]([CH3:49])[C:28]2[O:34][C:33]3[C:35]([Cl:45])=[CH:36][C:37]([N:39]4[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]4)=[CH:38][C:32]=3[CH2:31][S:30](=[O:47])(=[O:46])[C:29]=2[CH:48]=1)=[O:24]>CN(C=O)C>[CH2:13]([O:20][C:1]([N:42]1[CH2:41][CH2:40][N:39]([C:37]2[CH:36]=[C:35]([Cl:45])[C:33]3[O:34][C:28]4[C:27]([CH3:49])=[CH:26][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:48][C:29]=4[S:30](=[O:46])(=[O:47])[CH2:31][C:32]=3[CH:38]=2)[CH2:44][CH2:43]1)=[O:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 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 11699783HCID 11699783, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
22 °C

Procedure

Carbonyl diimidazole (0.34 g, 0.021 mmol) was added to a solution of benzyl alcohol (0.2 g, 0.014 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, 0.228 g, 0.016 mmol) in DMF (2 mL) was added dropwise 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. Crude was crystallised using ethyl acetate to obtain the title compound. Yield: 0.093 g (53%); mp: 170-173° C.; 1H NMR (DMSO-d6, 300 MHz): δ2.47 (s, 3H, CH3), 3.25 (s, 4H, 2CH2), 3.52 (s, 4H, 2CH2), 3.85 (s, 3H, OCH3), 5.09 (s, 2H, CH2), 5.15 (s, 2H, CH2), 7.09 (s, 1H, Ar), 7.14 (s, 1H, Ar), 7.32 (m, 5H, Ar), 8.09 (s, 1H, Ar), 8.15 (s, 1H, Ar); MS: m/e (ES+) 572 (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. customCrude was crystallised

Sources & evidence

ORD record
ord-a93924529c2146168262b395be6eb65b
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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