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 1692316Notes

Reaction equation

HRID 1692316 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-31a111e3dbb34367ae4b516d49f66f06
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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