Water → HCID 58098670, compound

HRID 384249Notes

Reaction equation

HRID 384249 reaction equation
N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:20]3)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[NH:42][C:43](=[O:45])[CH3:44].CC1C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1.CCOC(C)=O>[C:43]([NH:42][C:41]1[CH:40]=[C:39]([NH:38][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:20]3)[C:14]([C:35](=[O:37])[NH2:36])=[CH:13][N:12]=2)[CH:48]=[CH:47][CH:46]=1)(=[O:45])[CH3:44]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7604m-AminoacetanilideHCID 58014797HCID 58014797, compound

Product 1

HCID 58098670HCID 58098670, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of benzyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (582 mg, 1.16 mmol), 3′-amino-acetanilide (210 mg, 1.40 mmol) and pTsOH (220 mg, 1.16 mmol) in dioxane (10 mL) was stirred at 100 C for 4 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl. During the washing white solids precipitated out, which were collected to give the titled compound (412 mg). MS 518.5 (M+H); UV 201.6, 249.8 nm.

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. customDuring the washing white solids precipitated out
  4. customwhich were collected

Sources & evidence

ORD record
ord-800bb623d00449e38a08f307663d78c1
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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