Diisopropylethylamine → HCID 67202699, 화합물

HRID 85166

반응식

HRID 85166 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[NH2:14][C:15]1[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:14][C:15]1[C:24]([NH:25][C:9](=[O:11])[C:8]2[C:3]([C:2]([F:1])([F:13])[F:12])=[CH:4][CH:5]=[N:6][CH:7]=2)=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 5718252,3-Diaminobenzoic acid methyl esterHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 67202699HCID 67202699, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

4-(Trifluoromethyl)nicotinic acid (88; 1.00 g, 5.23 mmol) was taken up in DMF (8 mL) along with methyl 2,3-diaminobenzoate (118; 0.86 g, 5.23 mmol), HATU (2.98 g, 7.84 mmol) and DIEA (1.82 mL, 10.5 mmol). The reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc, washed with water, dried (Na2SO4) and concentrated under reduced pressure to afford crude methyl 2-amino-3-(4-(trifluoromethyl)nicotinamido)benzoate. This material was taken up in 5 mL of glacial acetic acid and stirred at 60° C. for 18 h. The reaction mixture was stirred at 90° C. for an additional 8 h. It was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with EtOAc, washed with dilute aqueous NaHCO3, dried (Na2SO4) and concentrated under reduced pressure to afford crude methyl 2-(4-(trifluoromethyl)pyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylate. This material was taken up in MeOH (8 mL) and H2O (8 mL) containing LiOH (0.4 g) and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and neutralized with 6 N HCl. The resulting solids were collected by filtration and dried to afford 570 mg of 2-(4-(trifluoromethyl)pyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid (35% yield from methyl 2,3-diaminobenzoate) 119. MS (ESI) calcd for C14H8F3N3O2: 307.06; found: 308 [M+H].

후처리

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f81df967852842778abb14a885aa6686
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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