p-Toluenesulfonic acid → HCID 59590140, compound

HRID 1971566Notes

Reaction equation

HRID 1971566 reaction equation
C(OC(=O)[NH:7][CH2:8][C@@H:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:37]=[C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]4[CH:36]=[CH:35][C:30]5[O:31][CH2:32][CH2:33][O:34][C:29]=5[CH:28]=4)[N:21]3[N:20]=2)=[CH:14][CH:13]=1)C)(C)(C)C.[CH3:39]C1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[NH2:7][C@@H:8]([CH3:39])[CH2:9][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:37]=[C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]4[CH:36]=[CH:35][C:30]5[O:31][CH2:32][CH2:33][O:34][C:29]=5[CH:28]=4)[N:21]3[N:20]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68705361HCID 68705361, compound

Product 1

HCID 59590140HCID 59590140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((S)-2-{4-[5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenoxy}-propyl)-carbamic acid tert-butyl ester (100 mg, 0.196 mmol) was dissolved in dichloromethane (4 ml) and MP-TsOH (1 g, 3.23 mmol) added. The mixture was shaken overnight at room temperature. The resin was collected by filtration and washed with methanol. The product was then cleaved from the resin with 2M ammonia in methanol. The eluant was concentrated in vacuo and the product was purified by prep LCMS.

Workup

  1. filtrationThe resin was collected by filtration
  2. washwashed with methanol
  3. concentrationThe eluant was concentrated in vacuo
  4. customthe product was purified by prep LCMS

Sources & evidence

ORD record
ord-ecd03987868d434a9b265cfaf7cc8a04
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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