tert-Butanol → HCID 58563674、化合物

HRID 241944ノート

反応式

HRID 241944 の反応式
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9](C(O)=O)[CH:10]=[C:3]12.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([O:42][C:19](=[O:28])[NH:16][C:9]1[CH:10]=[C:3]2[C:2](=[O:1])[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=1)([CH3:41])([CH3:40])[CH3:39]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 226053224-oxo-4H,5H,6H,7H-pyrazolo[1,5-a]pyridine-2- carboxylic acid

生成物 1

HCID 58563674HCID 58563674、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-2-carboxylic acid (2.56 g, 14.2 mmol, prepared according to EP1241170) in 160 mL dry toluene is added triethylamine (2.38 mL, 17.1 mmol) and diphenylphosphoryl azide (3.68 mL, 17.1 mmol) and the reaction mixture is stirred overnight at RT. Then tert-butanol (26.7 mL, 74.1 mmol) is added and the reaction is heated to 120° C. for 5 h. The solvents are removed under reduced pressure and the residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane). Yield: 2.32 g. HPLC-MS: Rt=1.55 min, (M+H-56)+=196. 1H NMR (DMSO-d6): δ 9.8 (s, 1H), 6.7 (s, 1H), 4.2 (t, 2H), 2.6 (t, 2H), 2.3 (quint, 2H), 1.4 (s, 9H).

後処理

  1. temperaturethe reaction is heated to 120° C. for 5 h
  2. customThe solvents are removed under reduced pressure
  3. customthe residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-8fc1b93c6591466885934fcbc3b18f93
出典データセット
uspto-grants-2014_02
特許番号
US08653097B2

反応ノート

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