[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid → HCID 178472930, 화합물

HRID 1363713노트

반응식

HRID 1363713 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].[CH3:17][CH:18]([CH3:29])[CH2:19][CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH3:28])[CH2:24][CH2:23]1.C1(N(CCC2C=CC=CC=2)C(=O)NC2SC(SC[C:46](O)=[O:47])=CN=2)CCCCC1>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH:15][C:46]([N:21]([CH2:20][CH2:19][CH:18]([CH3:29])[CH3:17])[C@H:22]2[CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][CH2:27]2)=[O:47])=[N:12][CH:11]=1)(=[O:8])=[O:9])[CH3:2]

참가 물질

6

반응물 3

HCID 11993791[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acidHCID 213556364-methyl-N-(3-methylbutyl)cyclohexan-1-amineHCID 86253773(2-Amino-thiazole-5-sulfonylamino)acetic acid ethyl ester

생성물 1

HCID 178472930HCID 178472930, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethyl-ureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals.

후처리

  1. temperaturecooled to room temperature
  2. customprepared
  3. additionwas added
  4. customThe reaction mixture was quenched with water
  5. customThe organic phase was isolated
  6. extractionthe aqueous phase was extracted with CH2Cl2
  7. customthe combined organic phases were dried
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in MeCN
  10. custompurified

출처 및 근거

ORD 기록
ord-9f7628796a88449698d17f9929bd4a6c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884210B2

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