Trifluoroacetic acid → HCID 10314436, compound

HRID 11570Notes

Reaction equation

HRID 11570 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].C(OC(=O)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][C:27]([C:29]1[S:30]C(CN)=[CH:32][CH:33]=1)=[O:28])(C)(C)C.F[C:38](F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][C:27]([C:29]1[S:30][C:11]([CH2:12][NH:8][C:1]([NH:3][CH2:7][C:6]#[CH:38])=[O:2])=[CH:32][CH:33]=1)=[O:28]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 69655378{2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Product 1

HCID 10314436HCID 10314436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15.8 mg (0.288 mmol) in 1 ml THF were added 46.7 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 1 h at rt. 1.7 ml trifluoroacetic acid were added and after 16 h at rt sat. aqueous NaHCO3 was added carefully and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was purified by HPLC/MS to yield 75 mg (0.228 mmol 5-[(3-Prop-2-ynyl-ureido)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide; exact MW [M+H] calc'd: 329.11; MW found [M+H]: 329.3.

Workup

  1. additionwas added carefully
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customthe solvent was evaporated
  5. customThe residue was purified by HPLC/MS

Sources & evidence

ORD record
ord-e05e980ae8ac4510ba2589fcb4989b89
Source dataset
uspto-grants-2006_08
Patent number
US07098247B2

Reaction notes

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