1,4-Dibromobutane → HCID 178526828, compound
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]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=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>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][C:29]([F:31])([F:30])[F:32])=[C:21]([CH:26]=1)[CH2:20][NH:19][C:12]1[N:11]=[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([N:1]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:7][CH2:6]2)[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-N2-[5-chloro-2-(trifluoromethoxy)benzyl]-5-nitropyrimidine-2,4-diamine (51 mg, 0.1 mmol) in DMF (0.5 mL) was added 1,4-dibromobutane (36 μL, 0.3 mmol) and DIPEA (104 μL, 0.6 mmol). The reaction mixture was stirred at 50° C. for 24 h and then 72 h at room temperature. The reaction mixture was then partitioned between EtOAc (20 mL) and saturated NaHCO3 (less than 1 mL). The organic phase was washed with water (2×2 mL) and dried over Na2SO4. The resulting residue was purified by preparative HPLC to afford 13 mg (25%) of the title compound as a yellow oily solid, m/z 529.3 [M+1]+
Workup
- custom72 h
- customat room temperature
- customThe reaction mixture was then partitioned between EtOAc (20 mL) and saturated NaHCO3 (less than 1 mL)
- washThe organic phase was washed with water (2×2 mL)
- dry with materialdried over Na2SO4
- customThe resulting residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-5db81b5e018847a680bdbb0cd548b10d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601714B2
Reaction notes
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