Water → HCID 178423436, compound

HRID 2237598Notes

Reaction equation

HRID 2237598 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]=[C:11]([NH2:20])[N:10]=1.[C:21]([O:25][C:26]([NH:28][C:29](N1C=CC=N1)=[N:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:27])([CH3:24])([CH3:23])[CH3:22].O>C(Cl)Cl>[NH2:20][C:11]1[N:10]=[C:9]([NH:8][C@H:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]2[NH:1][C:29]([NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])=[N:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 69241132HCID 69241132, compound

Product 1

HCID 178423436HCID 178423436, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.53 g of N4-[(1S,2R)-2-aminocyclohexyl]-6-methylquinazoline-2,4-diamine in 90 ml of methylene chloride, 5.18 g of N,N′-bis(t-butoxycarbonyl)-1H-pyrazole-1-carboxamidine was added, and then the mixture was stirred at room temperature for 15 hours. The reaction solution was mixed with water, extracted with methylene chloride and then dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 8.50 g of the desirable compound.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-56944cfceb6145a4b81f285161cce350
Source dataset
uspto-grants-2010_05
Patent number
US07718663B2

Reaction notes

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