Diisopropylethylamine → HCID 178450743, compound

HRID 1819434Notes

Reaction equation

HRID 1819434 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.Br[CH:33]([CH2:41][CH2:42]Br)[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:37]([O:36][C:34]([CH:33]1[CH2:41][CH2:42][N:1]1[C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:30])([F:31])[F:29])[N:11]=2)[CH2:6][CH2:7]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5107723tert-Butyl 2,4-dibromobutyrateHCID 178511544HCID 178511544, compound

Product 1

HCID 178450743HCID 178450743, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (300 mg, 0.69 mmol) in DMF (3 mL) were added t-butyl 2,4-dibromobutyrate (322 μL, 1.5 mmol) and DIPEA (297 μL), 1.7 mmol). The reaction mixture was stirred at 60° C. for 9 h. The reaction mixture was then diluted with EtOAc and washed with 1M Na2CO3, water (×4) and brine. The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 116 mg of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidine-2-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with 1M Na2CO3, water (×4) and brine
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-2a0fd2eb55be4801b8ee4b0f77394c2e
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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