Dimethylformamide → 2-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

HRID 1814013ノート

反応式

HRID 1814013 の反応式
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=[C:5]([CH2:17]O)[CH:4]=1)[CH3:2].CN(C)C=O.P(Cl)(Cl)([Cl:26])=O>C(Cl)Cl>[Cl:26][CH2:17][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 225043012-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

生成物 1

HCID 225042962-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (12-3, 0.146 g, 0.56 mmol) was stirred in anhydrous CH2Cl2 (2.5 mL) under N2. N,N-Dimethylformamide (0.043 mL, 0.56 mmol) was added followed by phosphorous oxychloride (0.209 mL, 2.24 mmol). After 2.5 hours, the reaction was concentrated and quenched by the addition of saturated NaHCO3 (aq). A precipitate formed which was filtered and washed with water to afford 2-{[4-(chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile as an orange solid. 1H NMR (DMSO-d6) δ 12.32 (s, 1H), 8.28 (s, 1H), 7.00 (d, 2H, J=3.66 Hz), 4.77 (s, 2H), 2.83 (q, 2H, J=7.63 Hz), 1.34 (t, 3H, J=7.63 Hz).

後処理

  1. concentrationthe reaction was concentrated
  2. customquenched by the addition of saturated NaHCO3 (aq)
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water

出典と根拠

ORDレコード
ord-5d62dfdcdef94cb6bc0aa01880df777e
出典データセット
uspto-grants-2005_04
特許番号
US06875767B2

反応ノート

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