1,4-Dibromobutane → HCID 178506372, compound

HRID 1819411Notes

Reaction equation

HRID 1819411 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][N:13]=[C:12]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][C:29]([F:32])([F:31])[F:30])[N:11]=2)[CH2:4][CH2:3]1.Br[CH2:34][CH2:35][CH2:36][CH2:37]Br.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[N:1]1([C@H:2]2[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]3[C:15]([C:16]([F:17])([F:18])[F:19])=[CH:14][N:13]=[C:12]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][C:29]([F:31])([F:32])[F:30])[N:11]=3)[CH2:6][CH2:7]2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 81531DiisopropylethylamineHCID 178511541HCID 178511541, compound

Product 1

HCID 178506372HCID 178506372, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-N2-[2-(trifluoromethoxy)benzyl]-5-(trifluoromethyl)pyrimidine-2,4-diamine (100 mg, 0.22 mmol) in DMF (2 mL) were added 1,4-dibromobutane (140 mg, 0.65 mmol) and DIPEA (113 μL, 0.65 mmol). The reaction mixture was stirred at room temperature for 16 h and then heated at 65° C. for another 2 h. The reaction mixture was then diluted with EtOAc and washed with water (×4). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 10:1 CH2Cl2:MeOH as an eluent to afford 49 mg of the title compound as a while solid, m/z 518.6 [M+1]+.

Workup

  1. temperatureheated at 65° C. for another 2 h
  2. washwashed with water (×4)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-de6b0fc73fe64fcb88e7a33bb3087bbf
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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