Ethylene Glycol → HCID 66602968, compound

HRID 2097401Notes

Reaction equation

HRID 2097401 reaction equation
C(O)CO.[CH2:5]([O:12][CH2:13][N:14]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH:30]3[CH2:32][CH2:31]3)[CH:20]=2)=[C:17]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[F:40])[C:16]([C:41]([O:43]CC)=O)=[C:15]1[CH:46]=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[NH2:49][NH2:50]>O>[CH2:5]([O:12][CH2:13][N:14]1[C:15]2[CH:46]=[N:49][NH:50][C:41](=[O:43])[C:16]=2[C:17]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[F:40])=[C:18]1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:27])[F:28])=[C:21]([O:29][CH:30]2[CH2:32][CH2:31]2)[CH:20]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24654Hydrazine hydrate (1:1)HCID 86627031ethyl 1-benzyloxymethyl-5-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4-(2-fluorobenzyl)-2-formyl-1H-pyrrol-3-carboxylate

Product 1

HCID 66602968HCID 66602968, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To 46 ml of ethylene glycol solution containing 5.01 g (8.44 mmol) of ethyl 1-benzyloxymethyl-5-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4-(2-fluorobenzyl)-2-formyl-1H-pyrrol-3-carboxylate obtained in the following Reference example 36-(f) was added 2.13 ml (42.5 mmol) of hydrazine monohydrate at 60° C., and then the mixture was stirred at 130° C. for 8.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=1:1→1:2 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 4.28 g of the title compound as a white solid. (Yield: 90%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer after separation
  4. washwas washed successively with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-b214e3c899ba4a15ab800e8ca3689869
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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