Pyridine, hydrofluoride (1:1) → 2-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

HRID 1814012ノート

反応式

HRID 1814012 の反応式
[Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][CH3:17])[N:13]=[C:12]([NH:18][C:19]2[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=2)[CH:11]=1)(C(C)(C)C)(C)C.N1C=CC=CC=1.F>C1COCC1>[CH2:16]([C:14]1[N:13]=[C:12]([NH:18][C:19]2[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=2)[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=1)[CH3:17]

参加物

4

反応物 2

HCID 64774Pyridine, hydrofluoride (1:1)2 回HCID 865882682-{[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-{[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (12-2) (0.225 g, 0.60 mmol) was dissolved in 2 mL THF. Hydrogen fluoride-pyridine (Aldrich, HF ˜70%, pyridine ˜30%) (0.060 mL) was added. After 1.5 hours, additional hydrogen fluoride-pyridine (0.50 mL) was added. After 2.5 hours the reaction was concentrated to remove THF and the residue was diluted with 1M aqueous K2CO3. The resulting precipitate was filtered and washed with water to afford the desired compound 12-3 as a yellow solid. 1H NMR (DMSO-d6) δ 12.19 (s, 1H), 8.26 (s, 1H), 6.96 (s, 1H), 6.86 (s, 1H), 4.51 (bs, 2H), 2.79 (q, 2H, J=7.63 Hz), 1.32 (t, 3H, J=7.63 Hz). [M+H]+=261.0816.

後処理

  1. concentrationAfter 2.5 hours the reaction was concentrated
  2. customto remove THF
  3. additionthe residue was diluted with 1M aqueous K2CO3
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water

出典と根拠

ORDレコード
ord-94f2a45adda14d90a89b09dfa167f2a5
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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