Hydrochloric Acid → HCID 66989640, compound

HRID 2407670Notes

Reaction equation

HRID 2407670 reaction equation
Br[CH2:2][CH2:3][OH:4].[Cl:5][C:6]1[CH:33]=[CH:32][C:9]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[O:25][N:24]=[C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:22]=3)[CH2:16][CH2:15]2)=[O:11])=[CH:8][C:7]=1[OH:34].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:5][C:6]1[CH:33]=[CH:32][C:9]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[O:25][N:24]=[C:23]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:22]=3)[CH2:16][CH2:15]2)=[O:11])=[CH:8][C:7]=1[O:34][CH2:2][CH2:3][OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 66989261HCID 66989261, compound

Product 1

HCID 66989640HCID 66989640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoethanol (0.012 mL) was added to a mixture of the compound prepared in Example 55 (50 mg) and potassium carbonate (49 mg) in N,N-dimethylformamide (0.8 mL). The mixture was stirred at room temperature overnight, then 50° C. for six hours. The reaction was cooled to room temperature and was adjusted to pH 7 via the addition of aqueous 3% hydrochloric acid. The mixture was extracted twice with ethyl acetate and the organic phases were combined, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (methanol:ethyl acetate=1:19) to obtain the title compound (10 mg) having the following physical data.

Workup

  1. wait50° C. for six hours
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (methanol:ethyl acetate=1:19)

Sources & evidence

ORD record
ord-0436ef92d12e4f789eae80ddb1019113
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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