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Methylamine → 2-(2-(4-(1-(methylamino)ethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162763
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HRID 1162763 반응식
[CH3:1][NH2:2].C1COCC1.[C:8]([C:11]1[C:12]([C:32]([F:35])([F:34])[F:33])=[N:13][N:14]([CH2:16][C:17]([NH:19][C:20]2[S:24][C:23]3[CH2:25][CH2:26][CH2:27][CH2:28][C:22]=3[C:21]=2[C:29]([NH2:31])=[O:30])=[O:18])[CH:15]=1)(=O)[CH3:9].[Na]>C(O)(=O)C.CO>[CH3:1][NH:2][CH:8]([C:11]1[C:12]([C:32]([F:34])([F:35])[F:33])=[N:13][N:14]([CH2:16][C:17]([NH:19][C:20]2[S:24][C:23]3[CH2:25][CH2:26][CH2:27][CH2:28][C:22]=3[C:21]=2[C:29]([NH2:31])=[O:30])=[O:18])[CH:15]=1)[CH3:9]
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참가 물질

7

반응물 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 595205152-(2-(4-acetyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

생성물 1

HCID 595205242-(2-(4-(1-(methylamino)ethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide수율 14%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

To MeOH (1.5 mL) was added 2M methylamine in THF (0.724 mL, 1.448 mmol). Acetic acid was added to the mixture to adjust the pH to 4-5. 2-(2-(4-acetyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (50 mg, 0.121 mmol) and sodium cyanoborohyde (7.58 mg, 0.121 mmol) were added before heating the reaction to 100° C. for 30 min by microwave irradiation. The reaction mixture was quenched with water before purification by preparative reverse phase HPLC. The product fractions were acidified to pH 3 with acetic acid before applying to a strong cation exchange cartridge (500 mg). The cartridge was washed with DCM/MeOH (1:1) before eluting the product with 2M NH3 in MeOH. The solvent was removed in vacuo to give the title compound (7.1 mg, 0.017 mmol, 14%).

후처리

  1. temperaturebefore heating
  2. customthe reaction to 100° C. for 30 min
  3. customby microwave irradiation
  4. customThe reaction mixture was quenched with water before purification by preparative reverse phase HPLC
  5. washThe cartridge was washed with DCM/MeOH (1:1)
  6. washbefore eluting the product with 2M NH3 in MeOH
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-1b08c47067794f56a36fb454edb68163
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07820707B2

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