Trimethyl orthoformate → HCID 86729277, compound

HRID 1051500Notes

Reaction equation

HRID 1051500 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[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1.[CH:22](OC)(OC)OC>CN(C=O)C.Cl.C(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:22][N:9]([CH:10]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[C:3]=2[CH:4]=1

Participants

6

Reactant 2

HCID 9005Trimethyl orthoformateHCID 86729276HCID 86729276, compound

Product 1

HCID 86729277HCID 86729277, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((2-amino-5-bromophenyl)amino)pyrrolidine-1-carboxylate (320 mg, 0.938 mmol), HC(OCH3)3 (5 mL) in DMF (10 mL) was added concentrated HCl (two drops). The mixture was then stirred at room temperature for 16 h before concentration. The residue was then diluted with DCM (50 mL) and washed with saturated NaHCO3 solution (25 mL), water (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated to give the crude desired product (250 mg, Yield 80%) which was used on the next step without further purification. LCMS (m/z): 366.1 (M+1).

Workup

  1. washwashed with saturated NaHCO3 solution (25 mL), water (50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1fc2043a6ca44413864f9047f3f089b4
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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