Dimethylformamide → HCID 57731451、化合物

HRID 2234706ノート

反応式

HRID 2234706 の反応式
[CH3:1][N:2]([CH3:39])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:15][CH:16]=2)[N:8]=[N:7][C:6]=1[NH2:38])=[O:4].CN(C)C=O.[OH-].[K+]>CO>[CH3:39][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[N:8]=[N:7][C:6]=1[NH2:38])=[O:4]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 57731610HCID 57731610、化合物

生成物 1

HCID 57731451HCID 57731451、化合物収率 14.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Crude 3-amino-6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide (56.6 mg, 0.104 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL) and 50% w/v aqueous potassium hydroxide (0.2 mL) was added. After 5 hours, the reaction was quenched by addition of acetic acid (0.5 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 3-amino-6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide (5.7 mg, 14.1%, 3 steps). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.90 (s, 3H), 3.0 (s, 3H), 3.82 (s, 3H), 6.44 (s, 2H), 7.07 (dt, J=7.5 Hz, J=1.0 Hz, 1H), 7.13 (br d, J=7.5 Hz, 1H), 7.30 (dt, J=7.5 Hz, J=1.5 Hz, 1H), 7.61 (dd, J=7.5 Hz, J=2.0 Hz, 1H), 7.83 (d, J=2.5 Hz, 1H), 7.92 (s, 1H), 8.55 (d, J=2.0 Hz, 1H), 8.87 (d, J=2.5 Hz, 1H), 11.89 (s, 1H). MS: m/z 389 (M+H+).

後処理

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (0.5 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-6638841ca2f34d54beb5466f434d01eb
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

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