1,2-Dichloroethane → N-[2-(Carbamoylamino)-1-(2,3-dichlorophenyl)ethyl]-2-[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetamide

HRID 2402844ノート

反応式

HRID 2402844 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([Cl:27])[CH2:25][Cl:26].[CH:28]1[CH:29]=[CH:30][C:31]2[N:36](O)N=[N:34][C:32]=2[CH:33]=1.C(N(CC)C(C)C)(C)C.C[N:48]([CH:50]=[O:51])C>C(OCC)(=O)C>[C:50]([NH:34][CH2:32][CH:31]([NH:36][C:21](=[O:22])[CH2:20][N:10]1[C:11](=[O:19])[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:16])[F:17])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[C:30]1[CH:29]=[CH:28][CH:33]=[C:25]([Cl:26])[C:24]=1[Cl:27])(=[O:51])[NH2:48]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59536724[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

生成物 1

HCID 46917113N-[2-(Carbamoylamino)-1-(2,3-dichlorophenyl)ethyl]-2-[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetamide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Of the compound from Example 177A, 162 mg (0.46 mmol), 145 mg (0.51 mmol) of the compound from Example 153A, 107 mg (0.56 mmol) of EDC, 75 mg (0.56 mmol) of HOBt and 97 μl (0.56 mmol) of N,N-diisopropylethylamine were stirred in 5.4 ml of DMF at RT overnight. The solution was diluted with 150 ml of ethyl acetate and extracted in succession twice each with 1M hydrochloric acid and with 1M aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate and freed from the volatile components on a rotary evaporator. The residue was purified by preparative HPLC [Method 20]. The product fraction was freed from the solvents on a rotary evaporator and the residue was dried in an HV. This gave 163 mg (61% of theory) of the title compound.

後処理

  1. extractionextracted in succession twice each with 1M hydrochloric acid
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customfreed from the volatile components on a rotary evaporator
  4. customThe residue was purified by preparative HPLC [Method 20]
  5. customThe product fraction was freed from the solvents on a rotary evaporator
  6. customthe residue was dried in an HV

出典と根拠

ORDレコード
ord-378c7b76f2d64fa19802b8fb96f42fd7
出典データセット
uspto-grants-2014_08
特許番号
US08796324B2

反応ノート

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