Trimethyl orthoformate → HCID 69000277, compound

HRID 1632023Notes

Reaction equation

HRID 1632023 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[C:12]([F:26])=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[O:10])=[CH:5][CH:4]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[CH3:31]OC(OC)OC.[OH-].[NH4+]>C(O)(=O)C.O>[Cl:25][C:21]1[CH:20]=[C:19]([C:13]2[C:14]([O:17][CH3:18])=[CH:15][CH:16]=[C:11]([C:9]([C:6]3[CH:7]=[CH:8][C:3]([N:2]4[CH:31]=[N:29][N:28]=[N:27]4)=[CH:4][CH:5]=3)=[O:10])[C:12]=2[F:26])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 68788318HCID 68788318, compound

Product 1

HCID 69000277HCID 69000277, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of (4-amino-phenyl)-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-methanone hydrochloride synthesized above (0.4 g, 1.02 mmol) and sodium azide (0.2 g, 3.06 mmol) in glacial acetic acid (10 mL) was added trimethylorthoformate (0.32 g, 3.06 mmol). The reaction was stirred at room temperature for 3 h, diluted with cold water (60 mL), than basified with ammonium hydroxide solution (28%). Extracted with dichloromethane (2×40 mL), the combined dichloromethane solution was washed with brine (40 ml), dried with Na2SO4, filtered, and concentrated to afford 0.38 g (90%) of (3′-chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-(4-tetrazol-1-yl-phenyl)-methanone as light yellow solid.

Workup

  1. extractionExtracted with dichloromethane (2×40 mL)
  2. washthe combined dichloromethane solution was washed with brine (40 ml)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c92a5148ada14dc9857f7ee8faab1719
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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