p-Toluenesulfonic acid → Tert-butyl 3-((2-(3-acetamidophenylamino)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate

HRID 533470Notes

Reaction equation

HRID 533470 reaction equation
N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]3)[C:14]([C:31](=[O:33])[NH2:32])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:34][C:35]1[CH:36]=[C:37]([CH:42]=[CH:43][CH:44]=1)[NH:38][C:39](=[O:41])[CH3:40].CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[C:39]([NH:38][C:37]1[CH:36]=[C:35]([NH:34][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20]3)[C:14]([C:31](=[O:33])[NH2:32])=[CH:13][N:12]=2)[CH:44]=[CH:43][CH:42]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7604m-AminoacetanilideHCID 66841163tert-butyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 58098654Tert-butyl 3-((2-(3-acetamidophenylamino)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylateYield 56.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate (118 mg, 0.260 mmol), 3′-amino-acetanilide (47 mg, 0.31 mmol) and pTsOH (57 mg, 0.30 mmol) in dioxane (2 mL) was stirred at 100 C for 18 h, during which time white solids precipitated out, which were collected and purified by HPLC to give the titled compound (69 mg). MS 470.6 (M+H); UV 202.2, 248.6 nm.

Workup

  1. customprecipitated out
  2. customwhich were collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-ec689d5928984c45bb3c591648e6a764
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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