p-Toluenesulfonic acid → HCID 59589612, compound

HRID 1971541Notes

Reaction equation

HRID 1971541 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]3[N:23]=[C:24]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]3[N:23]=[C:24]([NH:26][C:27]([CH:29]4[CH2:30][CH2:31]4)=[O:28])[N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:32]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59589537HCID 59589537, compound

Product 1

HCID 59589612HCID 59589612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

({4-[2-(Cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-phenylcarbamoyl}-methyl)-carbamic acid tert-butyl ester (0.08 g, 0.17 mmol) was dissolved in dichloromethane (3 ml), microporous p-toluenesulfonic acid (0.16 g, 0.51 mmol) was added and the mixture was shaken overnight. The resin was washed several times with methanol, and then the product was cleaved from the resin using a 2M ammonia/methanol solution. This solution was concentrated in vacuo to give clean product. LCMS method: 2, RT: 1.86 min, MI: 351 [M+1]. NMR (1H, DMSO, 300 MHz): 11.04 (brs, 1H), 8.02 (d, 2H), 7.82 (d, 2H), 7.66 (m, 2H), 7.28 (dd, 1H), 3.34 (brs, 2H), 2.03 (brs, 1H), 0.82 (d, 4H).

Workup

  1. washThe resin was washed several times with methanol
  2. concentrationThis solution was concentrated in vacuo
  3. customto give clean product

Sources & evidence

ORD record
ord-65a7ec0265074a4c918174f2ffa8290c
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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