Proton sponge → tert-butyl ({4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyanophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

HRID 46352

반응식

HRID 46352 반응식
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]([C:24]3[N:25]=[CH:26][S:27][CH:28]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:15])=[O:14])=[CH:9][C:8]=2[C:29]#[N:30])=[C:4]([C:33]2[N:37]([CH:38]3[CH2:41][N:40](C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:39]3)[N:36]=[CH:35][CH:34]=2)[CH:3]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.ClC(OC(Cl)C)=O>ClCCl>[NH:40]1[CH2:39][CH:38]([N:37]2[C:33]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:32]=[CH:31][C:5]=3[O:6][C:7]3[CH:12]=[CH:11][C:10]([S:13]([N:16]([C:24]4[N:25]=[CH:26][S:27][CH:28]=4)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21])(=[O:15])=[O:14])=[CH:9][C:8]=3[C:29]#[N:30])=[CH:34][CH:35]=[N:36]2)[CH2:41]1

참가 물질

5

반응물 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 59436484tert-butyl {[4-(4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamate

생성물 1

HCID 59436550tert-butyl ({4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyanophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-butyl {[4-(4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamate, (Preparation 680, 224 mg, 0.287 mmol) was dissolved in dichloromethane (10 ml) and N,N,N′,N′-tetramethylnaphthalene-1,8-diamine (150 mg, 0.70 mmol) was added, followed by 1-chloroethyl chloroformate (0.07 ml, 0.65 mmol) and the solution was stirred at room temperature for 3.5 hours. Concentrated in vacuo and the residue was dissolved in methanol (10 ml) and refluxed for 4 hours. Concentrated in vacuo to give the crude title compound as a brown gum, 200 mg. This material was used without purification in Example 815.

후처리

  1. concentrationConcentrated in vacuo
  2. dissolutionthe residue was dissolved in methanol (10 ml)
  3. temperaturerefluxed for 4 hours
  4. concentrationConcentrated in vacuo

출처 및 근거

ORD 기록
ord-e1f1e777542a4ca98bf16d7fa4e9f797
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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