Diisopropylethylamine → 6-[2-[4-methoxy-7-(3-methyl-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-oxo-acetyl]-2-oxo-1-phenyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile

HRID 885071노트

반응식

HRID 885071 반응식
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)=[C:5]2[NH:15][CH:16]=[C:17]([C:18](=[O:22])[C:19]([OH:21])=O)[C:4]=12.[O:23]=[C:24]1[C:33]([C:34]#[N:35])=[CH:32][C:31]2[CH2:30][NH:29][CH2:28][CH2:27][C:26]=2[N:25]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)=[C:5]2[NH:15][CH:16]=[C:17]([C:18](=[O:22])[C:19]([N:29]3[CH2:28][CH2:27][C:26]4[N:25]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:24](=[O:23])[C:33]([C:34]#[N:35])=[CH:32][C:31]=4[CH2:30]3)=[O:21])[C:4]=12

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 580260402-Oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrileHCID 596815922-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

생성물 1

HCID 445556026-[2-[4-methoxy-7-(3-methyl-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-oxo-acetyl]-2-oxo-1-phenyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile수율 4.42%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (70 mg, 0.232 mmol), 2-oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile (58.4 mg, 0.232 mmol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (90 mg, 0.279 mmol) in DMF (2 mL) was added N,N-diisopropylethylamine (0.406 mL, 2.324 mmol). The mixture was stirred at room temperature for 4 hours, and diluted with EtOAc (100 mL) and washed with 5% of NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by prep. HPLC and silica gel column (using EtOAc) to give 6-(2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetyl)-2-oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile (6.1 mg, 10.27 μmol, 4.42% yield). LCMS: m/z 535.09 (M+H)+, 1.65 min (method 7). 1H NMR (500 MHz, chloroform-d) δ ppm 11.07 (s, 1H) 9.05-9.12 (m, 1H) 8.18-8.27 (m, 1H) 7.45-7.78 (m, 5H) 7.14-7.21 (m, 2H) 4.50-4.73 (m, 2H) 3.95-4.04 (m, 3H) 3.64-3.90 (m, 2H) 2.53-2.57 (m, 3H) 2.42-2.50 (m, 2H).

후처리

  1. washwashed with 5% of NaHCO3 (20 mL), and brine (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by prep

출처 및 근거

ORD 기록
ord-ddd63eb0d7b044b9bbb0a6aeac628957
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242124B2

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