Diisopropylethylamine → HCID 90038500, compound

HRID 713202Notes

Reaction equation

HRID 713202 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].Cl.[F:14][C:15]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:16]=1[O:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:8][C:7]1[N:6]=[C:5]2[CH:9]=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[N:21]1[CH2:20][CH2:19][CH:18]([O:17][C:16]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:15]=2[F:14])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazineHCID 429489434-(2,4-Difluorophenoxy)piperidine hydrochloride

Product 1

HCID 90038500HCID 90038500, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-dichloropyrido[3,4-b]pyrazine (492 mg, 2.460 mmol) in DCM (5 mL) at 0° C. was treated with 4-(2,4-difluorophenoxyl)piperidine hydrochloride (676 mg, 2.71 mmol) and DIPEA (1.29 mL, 7.38 mmol). The reaction mixture was allowed to stir overnight, gradually warming to room temperature. The reaction mixture was quenched with the addition of saturated aqueous NH4Cl and was extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using a gradient of 20% to 60% EtOAc in heptanes to give the title compound as a pale yellow solid (736.2 mg, 79%). ESI-MS m/z [M+H]+ 377.4.

Workup

  1. customThe reaction mixture was quenched with the addition of saturated aqueous NH4Cl
  2. extractionwas extracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-e49d9f5feae5477586780b89f60c6a8f
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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