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

HRID 1253529ノート

反応式

HRID 1253529 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-28d4234df1ab4b9897dcedc0fa6812f2
出典データセット
uspto-grants-2013_06
特許番号
US08455477B2

反応ノート

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