p-Toluenesulfonic acid → HCID 136351519, compound

HRID 341226Notes

Reaction equation

HRID 341226 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)=O.Cl.[NH2:28][OH:29].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:29][N:28]=[CH:1][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57497682HCID 57497682, compound

Product 1

HCID 136351519HCID 136351519, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 1-[3-(7-Formyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (50 mg, 0.14 mmol) in toluene (5 ml) was added hydroxylamine hydrochloride (11 mg, 0.15 mmol) and triethylamine (21 μl, 0.15 mmol). The reaction mixture was stirred for 10 min before tosic acid (3 mg, 0.014 mmol) was added and then stirred for a further 18 h. The resulting precipitate was filtered off and washed with Et2O to give the product (23 mg). MS: [M+H]+ 378.

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-eaf3f9cebb88487086903e709b46839d
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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