Diisopropylethylamine → HCID 178526827, compound

HRID 1819472Notes

Reaction equation

HRID 1819472 reaction equation
[N+:1]([C:4]1[C:5](SC#N)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].[NH2:26][CH2:27][C@@H:28]1[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[N+:1]([C:4]1[C:5]([NH:26][CH2:27][C@@H:28]2[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:21])([F:20])[F:22])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57885541(5-Nitro-4-thiocyanato-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amineHCID 178511286HCID 178511286, compound

Product 1

HCID 178526827HCID 178526827, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Nitro-4-thiocyanato-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amine (10 g, 26.9 mmol) was dissolved in DCM (100 ml). cis-4-aminomethyl-cyclohexanol (3.48 g, 26.9 mmol) and diisopropylethylamine (10 mL, 53.8 mmol) were added to the solution and stirred overnight. The reaction mixture was evaporated in-vacuo and purified by column chromatography (1% MeOH/99% CH2Cl2). The resulting solid was washed with cold methanol to give a pale yellow solid as cis-4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexanol (11.3 g, 25.6 mmol, 95.1%).

Workup

  1. customThe reaction mixture was evaporated in-vacuo
  2. custompurified by column chromatography (1% MeOH/99% CH2Cl2)
  3. washThe resulting solid was washed with cold methanol

Sources & evidence

ORD record
ord-594009d0a8cf42a3b072e0d281ad53f2
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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