HCID 10407249, compound → HCID 10378795, compound

HRID 750751Notes

Reaction equation

HRID 750751 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[S:20][C:21]([C:24](=[O:26])[NH2:25])=[C:22]([NH2:23])[C:15]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.C(Cl)Cl>C(Cl)Cl>[NH2:23][C:22]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][C:14]=2[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[S:20][C:21]=1[C:24]([NH2:25])=[O:26]

Participants

4

Reactant 2

HCID 10407249HCID 10407249, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 10378795HCID 10378795, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 18 mg 4-(3-amino-2-carbamoyl-thieno[2,3-b]pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 1 mL CH2Cl2+1 mL trifluoroacetic acid was stirred with a drying tube for 4 h at room temperature. The reaction was concentrated in vacuo and developed prep plate in 25% MeOH—CH2Cl2-2% NH4OH and the band was eluted with 50% MeOH—CH2Cl2 to get an oil that was re-dissolved 10% MeOH—CH2Cl2, filtered, concentrated, and dried in vacuo at 60° C. to provide 4.6 mg of the product as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washthe band was eluted with 50% MeOH—CH2Cl2
  3. customto get an oil that
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-03228ab6e97146b58cce204d00a060e2
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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