1,3-Dibromopropane → HCID 178510353, compound

HRID 1819417Notes

Reaction equation

HRID 1819417 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]#[N:17])=[CH:14][N:13]=[C:12]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][C:27]([F:30])([F:29])[F:28])[N:11]=2)[CH2:4][CH2:3]1.Br[CH2:32][CH2:33][CH2:34]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]#[N:17])=[CH:14][N:13]=[C:12]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][C:27]([F:29])([F:30])[F:28])[N:11]=3)[CH2:6][CH2:7]2)[CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 81531DiisopropylethylamineHCID 178510354HCID 178510354, compound

Product 1

HCID 178510353HCID 178510353, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-{[(trans-4-aminocyclohexyl)methyl]amino}-2-{[2-(trifluoromethoxy)benzyl]-amino}pyrimidine-5-carbonitrile (150 mg, 0.36 mmol) in DMF (1 mL) were added 1,3-dibromo-propane (86 mg, 0.43 mmol) and DIPEA (124 μL, 0.71 mmol). The reaction mixture was stirred at 50° C. for 24 h. The reaction mixture was then diluted with EtOAc and washed with NaHCO3 (×1) and 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 10:1:0.2 CH2Cl2:MeOH:NH4OH as an eluent to afford 54 mg (33%) of the title compound as a white solid, m/z 461.6 (M+1)+.

Workup

  1. washwashed with NaHCO3 (×1) and water (×4)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-ac409ed5006a4ec383d6ee8d043c7739
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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