Ethyl Acetate → HCID 73775810、化合物

HRID 1405951ノート

反応式

HRID 1405951 の反応式
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[N:12]([C:15]1[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:18]=[C:17]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:16]=1)=[C:13]=[O:14].CCOC(C)=O>C(Cl)Cl>[F:26][C:23]([F:24])([F:25])[CH2:22][O:21][C:19]1[CH:18]=[C:17]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:16]=[C:15]([NH:12][C:13](=[O:14])[N:2]([CH3:1])[C:3]2[S:4][C:5]([C:8]([F:10])([F:9])[F:11])=[CH:6][CH:7]=2)[N:20]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 576517972-Isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidineHCID 86718388N-Methyl-5-(trifluoromethyl)thiophen-2-amine

生成物 1

HCID 73775810HCID 73775810、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-methyl-5-(trifluoromethyl)thiophen-2-amine in CH2Cl2 (2 mL) was added 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (1.6 mL, 1.0 M in THF) (prepared as described in U.S. Pat. No. 8,013,154, the contents of which were incorporated herein above by reference in their entirety). This reaction was stirred at ambient temperature overnight. TLC indicated the reaction was complete. The solvent was removed under reduced pressure and the residue was purified using normal phase chromatography which afforded product (471 mg, 56% over three steps) as an off-white solid, mp 99-101° C.: Rf=0.26 (30% EtOAc, hex); 1H NMR (DMSO-d6) 10.34 (s, 1H), 7.48 (d, 1H, J=3.3 Hz), 6.78 (d, 1H, J=4.3 Hz), 6.28 (s, 1H), 5.02 (q, 4H, J=17.8, 8.9 Hz), 3.49 (s, 3H); ESIMS m/z 497 [(M−1)+].

後処理

  1. customprepared
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified
  4. customafforded product (471 mg, 56% over three steps) as an off-white solid, mp 99-101° C.

出典と根拠

ORDレコード
ord-174319afdb7f47dab3d19b4c1746af68
出典データセット
uspto-grants-2014_12
特許番号
US08916578B2

反応ノート

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