Water → HCID 11578091, compound

HRID 507089Notes

Reaction equation

HRID 507089 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][OH:10].[F:11][C:12]([F:50])([F:49])[C:13]1[CH:14]=[C:15]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:16][N:17]([C:37]1[NH:41][N:40]=[N:39][N:38]=1)[C@H:18]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[C:20]2[C:31]([CH3:36])=[C:32]([CH3:35])[CH:33]=[CH:34][C:19]1=2.O>CN(C=O)C.C(OCC)(=O)C>[F:46][C:45]([F:48])([F:47])[C:43]1[CH:42]=[C:15]([CH:14]=[C:13]([C:12]([F:49])([F:11])[F:50])[CH:44]=1)[CH2:16][N:17]([C:37]1[N:38]=[N:39][N:40]([CH2:8][CH2:9][OH:10])[N:41]=1)[C@H:18]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[C:20]2[C:31]([CH3:36])=[C:32]([CH3:35])[CH:33]=[CH:34][C:19]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178422535HCID 178422535, compound

Product 1

HCID 11578091HCID 11578091, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Add potassium carbonate (58 mg, 0.42 mmol) and 2-bromoethanol (0.038 mL, 0.53 mmol) to a solution of (S)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-8,9-dimethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (Example 56, Step 5) (120 mg, 0.21 mmol) in DMF (0.4 mL) at room temperature in a tube. Seal the tube and stir the mixture at 50° C. for 3 h. Cool the mixture at room temperature and add water and ethyl acetate. Separate the layers, dry the organic phase over anhydrous Na2SO4, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexane/ethyl acetate, to provide 58 mg (45%) of the title compound. MS (ES+): 615 (M+H).

Workup

  1. customSeal the tube
  2. temperatureCool the mixture at room temperature
  3. customSeparate the layers
  4. dry with materialdry the organic phase over anhydrous Na2SO4
  5. filtrationfilter
  6. customremove the solvent under reduced pressure
  7. customPurify the residue by flash chromatography
  8. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-7dab761bdef04d2e923f39f531f9774c
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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