Trifluoroacetic acid → HCID 57525637、化合物

HRID 1594403ノート

反応式

HRID 1594403 の反応式
[C:1]([N:5]1[C:9]([NH2:10])=[CH:8][C:7]([CH:11]2[CH2:14][C:13]([O:17][CH3:18])([O:15][CH3:16])[CH2:12]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26](O)([C:28]([F:31])([F:30])[F:29])=[O:27].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[C:1]([N:5]1[C:9]([NH:10][C:26](=[O:27])[C:28]([F:31])([F:30])[F:29])=[CH:8][C:7]([CH:11]2[CH2:12][C:13]([O:15][CH3:16])([O:17][CH3:18])[CH2:14]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 57525626HCID 57525626、化合物

生成物 1

HCID 57525637HCID 57525637、化合物収率 60%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a stirring solution of 2-tert-butyl-5-(3,3-dimethoxy-cyclobutyl)-2H-pyrazol-3-ylamine (5.0 g, 19.7 mmol) in EtOAc (40 mL) was added triethylamine (27 mL, 197 mmol), TFA (2.3 mL, 29.6 mmol), followed by a solution of 1-propanephosphonic acid cyclic anhydride (25 mL, 50 wt % sol. in EtOAc, 39.4 mmol). After 72 hr, the reaction was diluted with EtOAc and washed with aqueous NaOH (1 N). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by MPLC, using a Biotage® column (35 L), eluting with 25% EtOAc/hexanes. The product-containing fractions were collected and concentrated to yield the title compound (4.1 g, 60% yield) as a colorless oil. 400 MHz 1H NMR (CDCl3) d 8.00 (bs, 1H), 6.26 (s, 1H), 3.22 (dddd, J=8.7, 8.7, 8.7, 8.7, Hz, 1H), 3.18 (s, 3H), 3.15 (s, 3H), 2.61-2.55 (m, 2H), 2.25-2.19 (m, 2H), 1.59 (s, 9H). LRMS m/z (APCI+) 350 (M+1).

後処理

  1. washwashed with aqueous NaOH (1 N)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of this material
  6. washeluting with 25% EtOAc/hexanes
  7. customThe product-containing fractions were collected
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-915751c0add54f78a2a02dc66c6370a3
出典データセット
uspto-grants-2007_11
特許番号
US07300944B2

反応ノート

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