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

HRID 1814012노트

반응식

HRID 1814012 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-94f2a45adda14d90a89b09dfa167f2a5
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875767B2

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