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 1402019Notes

Reaction equation

HRID 1402019 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-96866f7ad13e429bb212f233d4b88408
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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