Water → HCID 178501268, 화합물

HRID 1035743노트

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HRID 1035743 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 178501268HCID 178501268, 화합물수율 38.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-f4185056347f494695c4c9a037c8deb8
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546391B2

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