1,4-Dibromobutane → HCID 178478285, compound

HRID 1623384Notes

Reaction equation

HRID 1623384 reaction equation
[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[N:20][C:19]([Cl:22])=[C:18]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:17]=2)=[CH:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][CH2:39][CH2:40][CH2:41]Br>CN(C=O)C>[Cl:22][C:19]1[C:18]([NH:23][CH2:24][CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[N:17][C:16]([C:3]2[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH:8][C@H:9]3[CH2:14][CH2:13][C@H:12]([N:15]4[CH2:41][CH2:40][CH2:39][CH2:38]4)[CH2:11][CH2:10]3)[CH:4]=2)=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178511595HCID 178511595, compound

Product 1

HCID 178478285HCID 178478285, compoundYield 23.07%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a scintillation vial containing trans-N1-(5-chloro-4-(5-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazin-2-yl)pyridin-2-yl)cyclohexane-1,4-diamine (12 mg, 0.027 mmol) and K2CO3 (3.67 mg, 0.027 mmol) was added DMF (1 ml) and 1,4-dibromobutane (3.15 μl, 0.027 mmol). The reaction mixture was capped and heated to 60° C. for 3 hr. The crude solution was concentrated and purified by reverse phase preparative HPLC to yield 3-chloro-6-(5-chloro-2-(trans-4-(pyrrolidin-1-yl)cyclohexylamino)pyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (3.8 mg, 6.13 μmol, 23.07% yield), LCMS (m/z): 505.2 (MH+), retention time=0.64 min, and a TFA salt after lyapholization.

Workup

  1. customThe reaction mixture was capped
  2. concentrationThe crude solution was concentrated
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-6274d45b507e40baaeaedec25218d83e
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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