Trimethyl orthoformate → HCID 86729274, compound

HRID 1399870Notes

Reaction equation

HRID 1399870 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1.[CH:21](OC)(OC)OC>CN(C=O)C.Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:21][N:9]([CH:10]3[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]3)[C:3]=2[CH:4]=1

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 86729273HCID 86729273, compound

Product 1

HCID 86729274HCID 86729274, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-((2-amino-5-bromophenyl)amino)azetidine-1-carboxylate (320 mg, 0.938 mmol), HC(OCH3)3 (5 mL) in DMF (10 mL) was added concentrated HCl (two drops). The reaction mixture was stirred at room temperature for 16 h then concentrated and diluted with DCM (50 mL) and washed with saturated NaHCO3 solution (25 mL). The organic layer was washed with water (50 mL) and dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated to yield a crude desired product (250 mg, Yield 80%) which was used in the next step without further purification. LCMS (m/z): 352.1 (M+1).

Workup

  1. concentrationthen concentrated
  2. additiondiluted with DCM (50 mL)
  3. washwashed with saturated NaHCO3 solution (25 mL)
  4. washThe organic layer was washed with water (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3720a13c649a496383161d8b334ce2c8
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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