Water → tert-butyl [2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzyl]carbamate

HRID 1500059ノート

反応式

HRID 1500059 の反応式
[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[CH3:19][N:20]1[C:24]([C:25](O)=[O:26])=[C:23]([C:28]([F:31])([F:30])[F:29])[C:22]([C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[N:21]1.[NH2:39][C:40]1[CH:41]=[CH:42][C:43]([Cl:55])=[C:44]([CH:54]=1)[CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50].O>C1COCC1>[Cl:55][C:43]1[CH:42]=[CH:41][C:40]([NH:39][C:25]([C:24]2[N:20]([CH3:19])[N:21]=[C:22]([C:32]([F:37])([F:38])[C:33]([F:35])([F:36])[F:34])[C:23]=2[C:28]([F:30])([F:31])[F:29])=[O:26])=[CH:54][C:44]=1[CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52]

参加物

6

反応物 4

HCID 962WaterHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21077619Tert-butyl (5-amino-2-chlorobenzyl)carbamateHCID 866600921-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 131734263tert-butyl [2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzyl]carbamate収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (=DMTMM, see Tetrahedron 1999, 55, 13159-13170) (1.25 g, 4.51 mmol, 1.1 eq.) was added to 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (1.28 g, 4.1 mmol; preparation according to WO2010/051926) and tert-butyl (5-amino-2-chlorobenzyl)carbamate (1.05 g, 4.1 mmol, 1.0 eq.) in THF (15 ml), and the mixture was left at room temperature for 18 h. Water (30 ml) was added, the mixture was extracted with ethyl acetate (3×30 ml) and the extracts were dried over MgSO4. After concentration under reduced pressure, the product was purified by column chromatography on silica gel (hexane/ethyl acetate), giving tert-butyl [2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzyl]carbamate (924 mg, 41%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (3×30 ml)
  2. dry with materialthe extracts were dried over MgSO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe product was purified by column chromatography on silica gel (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-cd729f0ec4364cedbaae3247b1a9251a
出典データセット
uspto-grants-2015_12
特許番号
US09204645B2

反応ノート

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