Methanol → HCID 71240866、化合物

HRID 1842715ノート

反応式

HRID 1842715 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[C:5]([Cl:17])=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:26]=[C:25]([C:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH:32]=2)[C:24]([N+:34]([O-:36])=[O:35])=[CH:23][C:21]=1[NH2:22].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CO>C1COCC1>[Cl:17][C:5]1[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:7][C:2]([NH:22][C:21]2[CH:23]=[C:24]([N+:34]([O-:36])=[O:35])[C:25]([C:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH:28]=3)=[CH:26][C:20]=2[O:19][CH3:18])=[N:3][CH:4]=1

参加物

6

反応物 4

HCID 887MethanolHCID 2733832Lithium HexamethyldisilazideHCID 592911623-(2,5-Dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine2 回HCID 866773252-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline2 回

生成物 1

HCID 71240866HCID 71240866、化合物収率 72.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 3-(2,5-dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (Intermediate 21, 575 mg, 1.86 mmol) and 2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline (Intermediate 3, 490 mg, 1.86 mmol) was stirred in THF (30 mL) and cooled in an ice/water bath. Lithium bis(trimethylsilyl)amide (4.10 mL, 4.10 mmol, 1M in THF) was then added dropwise and the mixture was stirred for 1 h. CH3OH was added and the mixture was concentrated in vacuo. The crude material was suspended in CH3OH and the mixture was filtered. The collected solid was washed with CH3OH and diethyl ether and dried on the filter to give the title compound (660 mg, 72%) as a yellow powder; 1H NMR: 2.29 (3H, s), 2.30-2.38 (2H, m), 2.58 (2H, t), 2.97 (2H, dd), 3.96 (3H, s), 5.60-5.68 (1H, m), 7.00 (1H, s), 7.16 (1H, td), 7.36-7.45 (1H, m), 8.49-8.56 (3H, m), 8.87 (1H, d), 8.90 (1H, s), 8.97 (1H, s); m/z: ES+ MH+ 492.4.

後処理

  1. temperaturecooled in an ice/water bath
  2. concentrationthe mixture was concentrated in vacuo
  3. filtrationthe mixture was filtered
  4. washThe collected solid was washed with CH3OH and diethyl ether
  5. customdried on the
  6. filtrationfilter

出典と根拠

ORDレコード
ord-a9ae075771974ec0b1d79ebe15e991bf
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

反応ノート

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