Cyclopropanecarboxaldehyde → HCID 178510350、化合物

HRID 40655

反応式

HRID 40655 の反応式
COC1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9]2[C:14]([NH2:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]3[N:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[CH:10]=2)=CC=1.C1(C=O)CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[CH:6]1([C:7]2[NH:8][C:9]3[CH:10]=[C:11]([NH:16][C:17]4[N:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=4)[N:12]=[CH:13][C:14]=3[N:15]=2)[CH2:25][CH2:26]1

参加物

5

反応物 3

HCID 123114CyclopropanecarboxaldehydeHCID 656671Sodium PyrosulfiteHCID 670174745-(4-(4-Methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrile

生成物 1

HCID 178510350HCID 178510350、化合物収率 16.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of crude 5-(4-(4-methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrile (0.083 mmol), cyclopropane carboxaldehyde (5.9 mg, 0.083 mmol) and sodium metabisulfite (16 mg, 0.083 mmol) in DMF (1 mL) was heated at 100° C. for 4 hours. Upon cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated to a light brown solid. The solid was stirred at 65° C. with trifluoroacetic acid. Upon completion of the reaction, the mixture was concentrated. Preparative HPLC gave the title compound (3.7 mg, 16%). 1H NMR (d6-DMSO, 400 MHz) δ 12.60 (br s, 1H), 10.75 (br s, 1H), 8.80 (s, 1H), 8.75 (s, 1H), 8.50 (s, 1H), 8.10 (s, 1H), 2.10-2.20 (m, 1H), 1.00-1.20 (m, 4H). LCMS (2) Rt=1.68 min; m/z (ESI−) 276 (M−H); (ESI+) 278 (MH+).

後処理

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a light brown solid
  6. customUpon completion of the reaction
  7. concentrationthe mixture was concentrated

出典と根拠

ORDレコード
ord-f3b59bc4629d4ec996117730bb0910e8
出典データセット
uspto-grants-2013_09
特許番号
US08530468B2

関連ノート

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