Diisopropylethylamine → 2-acetamido-N-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)isonicotinamide

HRID 623573

반응식

HRID 623573 반응식
Cl.Cl.[F:3][C:4]([F:16])([F:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24](O)=[O:25])(=[O:19])[CH3:18].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24]([NH:14][CH2:13][C:9]1[CH:8]=[C:7]([O:6][CH2:5][C:4]([F:3])([F:15])[F:16])[CH:12]=[CH:11][N:10]=1)=[O:25])(=[O:19])[CH3:18]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 37744662-Acetamidopyridine-4-carboxylic acidHCID 67510820(4-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanamine dihydrochloride

생성물 1

HCID 569660082-acetamido-N-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)isonicotinamide수율 38%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a mixture of (4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanamine dihydrochloride (20 mg, 0.070 mmol, Amine-2), 2-acetamidoisonicotinic acid (15 mg, 0.084 mmol) and N,N-diisopropylethylamine (0.049 mL, 0.28 mmol) in N,N-dimethylformamide (0.5 mL) is added a solution of HBTU (40 mg, 0.11 mmol) in N,N-dimethylformamide (0.5 mL) at room temperature. After stirring at room temperature for 2 hours, the mixture is poured into water (2 mL) and extracted with ethyl acetate (3 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then by preparative LC-MS to give 9.8 mg (38% yield) of the title compound.

후처리

  1. extractionextracted with ethyl acetate (3 mL)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-29829bd2666844e5b2e0022e1a8989de
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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