Acetic Acid → N-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}pyridin-3-amine

HRID 1253529노트

반응식

HRID 1253529 반응식
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH:18]=O)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[NH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH2:18][NH:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 100093-AminopyridineHCID 5049666Sodium triacetoxyborohydrideHCID 866570544-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

생성물 1

HCID 58404894N-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}pyridin-3-amine

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

A solution of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (10.0 mg, 0.039 mmol), 3-aminopyridine (5.5 mg, 0.059 mmol), and acetic acid (50 μl) in 1,2-dichloroethane (1 ml) was stirred for 2 d. Sodium triacetoxyborohydride (24.8 mg, 0.117 mmol) was added and the mixture was stirred for 1 d. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was filtered with isoElute and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to give N-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}pyridin-3-amine 1H NMR (500 MHz, CDCl3) δ 8.52 (s, 1H); 8.21 (s, 1H); 8.00 (d, 1H); 7.96 (s, 1H), 7.80 (s, 1H), 7.69 (d, 1H), 7.02 (d, 1H), 6.95 (d, 1H), 6.81 (s, 1H), 6.08 (t, 1H), 4.47 (s, 2H), 3.98 (s, 3H), 3.82 (s, 3H) LRMS (ESI) calculated for C18H19N6O [M+H]+, 335.2; found 335.1.

후처리

  1. washwashed with saturated aqueous sodium bicarbonate
  2. filtrationThe organic layer was filtered with isoElute and
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-28d4234df1ab4b9897dcedc0fa6812f2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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