Trifluoroacetic acid → HCID 10314436, 화합물

HRID 11570노트

반응식

HRID 11570 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 10314436HCID 10314436, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e05e980ae8ac4510ba2589fcb4989b89
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098247B2

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