Water → 5-{7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidin-5-yl}-2-(tert-butoxycarbonyl)-(1R)-2,5-diaza-bicyclo[2.2.1]heptane

HRID 897404Notes

Reaction equation

HRID 897404 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[C:4]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]([O:38][C:39]([N:41]1[CH2:46][C@H:45]2[CH2:47][C@@H:42]1[CH2:43][NH:44]2)=[O:40])([CH3:37])([CH3:36])[CH3:35].O>CN(C=O)C>[Cl:27][C:23]1[CH:22]=[C:21]([C:4]2[N:3]=[C:2]([N:44]3[CH2:43][C@H:42]4[CH2:47][CH:45]3[CH2:46][N:41]4[C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[N:7]3[CH:8]=[N:9][N:10]=[C:6]3[C:5]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[CH:12]=2)[CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11860399N-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 223466035-Chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Product 1

HCID 208169155-{7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidin-5-yl}-2-(tert-butoxycarbonyl)-(1R)-2,5-diaza-bicyclo[2.2.1]heptane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)-phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (820 mg, 2.0 mmole), potassium carbonate (ca. 1.0 g) and (−)-2-(tert-butoxycarbonyl)-(1R, 4R)-2,5-diaza-bicyclo[2.2.1]heptane (436 mg, 2.2 mmole) in 10 ml of DMF was stirred at room temperature for 16 hours. The reaction solution was poured into water (50 mL), and precipitate was filtered and washed with water and dried under vacuum to give product as off white solid; MS m/z (M)+ 572.3; C27H25ClF3N7O2 requir. 572.

Workup

  1. filtrationwas filtered
  2. washwashed with water
  3. customdried under vacuum
  4. customto give product as off white solid

Sources & evidence

ORD record
ord-3eceb919491a46659ec43915b1b11fbf
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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