Water → HCID 178501268、化合物

HRID 1035743ノート

反応式

HRID 1035743 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].[F:21][C:22]1[CH:23]=[C:24]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:25][C:26]1[S:30][C:29]([NH2:31])=[N:28][N:27]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[F:35][C:33]1[CH:32]=[C:24]([CH:23]=[C:22]([F:21])[CH:34]=1)[CH2:25][C:26]1[S:30][C:29]([NH:31][C:16]([C:15]2[CH:14]=[CH:13][C:12]([O:11][C@@H:8]3[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]3)=[CH:20][CH:19]=2)=[O:18])=[N:28][N:27]=1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 667401415-(3,5-Difluorobenzyl)-1,3,4-thiadiazol-2-amineHCID 178501272HCID 178501272、化合物

生成物 1

HCID 178501268HCID 178501268、化合物収率 38.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2.2 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (7.91 mmol, 1 eq.) are placed in 30 mL of dimethylformamide at room temperature. 1.98 g of 5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylamine (8.70 mmol, 1.1 eq.), 4.42 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (9.49 mmol, 1.2 eq.) and 2.76 mL of diisopropylethylamine (15.81 mmol, 2 eq.) are successively added. The reaction mixture is stirred for 6 days at room temperature, poured into water and extracted with ethyl acetate. The organic phase is washed three times with water and once with brine. The organic phase is concentrated and the residue is chromatographed on silica gel, eluting with a gradient of ethyl acetate in heptane ranging from 7% to 30%. 1.5 g of methyl cis-4-{4-[5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate are obtained.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed three times with water
  3. concentrationThe organic phase is concentrated
  4. customthe residue is chromatographed on silica gel
  5. washeluting with a gradient of ethyl acetate in heptane ranging from 7% to 30%

出典と根拠

ORDレコード
ord-f4185056347f494695c4c9a037c8deb8
出典データセット
uspto-grants-2013_10
特許番号
US08546391B2

反応ノート

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