Hydrochloric Acid → HCID 11599824, compound

HRID 507104Notes

Reaction equation

HRID 507104 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([OH:10])[CH3:9].[CH:11]([O:14][C:15]([N:17]1[C:30]2[C:22](=[CH:23][C:24]3[CH2:25][CH2:26][CH2:27][C:28]=3[CH:29]=2)[C@@H:21]([N:31]([CH2:37][C:38]2[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=2)[C:32]2[N:33]=[N:34][NH:35][N:36]=2)[CH2:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].Cl>CN(C)C=O>[CH:11]([O:14][C:15]([N:17]1[C:30]2[C:22](=[CH:23][C:24]3[CH2:25][CH2:26][CH2:27][C:28]=3[CH:29]=2)[C@@H:21]([N:31]([CH2:37][C:38]2[CH:39]=[C:40]([C:48]([F:49])([F:50])[F:51])[CH:41]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:43]=2)[C:32]2[N:33]=[N:34][N:35]([CH2:9][CH2:8][OH:10])[N:36]=2)[CH2:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14202443Ethanol, 1-bromo-2×HCID 59432468HCID 59432468, compound

Product 1

HCID 11599824HCID 11599824, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add potassium carbonate (40 mg, 0.29 mmol) and bromoethanol (0.018 mL, 0.26 mmol) to a solution of (S)-9-[(3,5-Bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-2,3,6,7,8,9-hexahydro-1H-5-aza-cyclohepta[f]indene-5-carboxylic acid isopropyl ester (50 mg, 0.086 mmol) in dimethylformamide (0.3 mL). Stir at room temperature for 18 hrs in a sealed tube. Then add bromoethanol (0.018 mL, 0.26 mmol) and stir for 2 hrs. Add a 1N solution of hydrochloric acid and extract with dichloromethane. Dry the organic phase over anhydrous sodium sulfate, filter and concentrate in vacuo. Purify the residue using silica gel cartridge, eluting with ethyl acetate/hexanes to afford the title compound (26 mg, 49%). MS (ES+): 627 (M+H).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry the organic phase over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue
  6. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e37f7e0a389b46b69bae3725ddddd44b
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…