Ammonium Chloride → 4-((1-(3-Chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)oxy)-3-fluorobenzonitrile

HRID 713203Notes

Reaction equation

HRID 713203 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].CCN(C(C)C)C(C)C.Cl.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[C:27]#[N:28].[NH4+].[Cl-]>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:36]1[CH2:35][CH2:34][CH:33]([O:32][C:31]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[F:23])[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazineHCID 1181593163-Fluoro-4-(piperidin-4-yloxy)benzonitrile hydrochloride

Product 1

HCID 1181591914-((1-(3-Chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)oxy)-3-fluorobenzonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dichloropyrido[3,4-b]pyrazine (1.00 g, 5.00 mmol) in DCM (10.0 mL) at 0° C. was added DIPEA (2.62 mL, 15.00 mmol) and 3-fluoro-4-(piperidin-4-yloxy)benzonitrile hydrochloride (1.283 g, 5.00 mmol). The reaction mixture was stirred for 30 min, warming gradually to room temperature. The reaction mixture was treated with saturated aqueous NH4Cl. The organic layer containing yellow solid was collected and concentrated under reduced pressure. The solid was filtered, washing with water, and was lyophilized overnight to give the title compound as a yellow solid (1.325 g, 69%). ESI-MS m/z [M+H]+ 384.3.

Workup

  1. additionThe organic layer containing yellow solid
  2. customwas collected
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe solid was filtered
  5. washwashing with water
  6. waitwas lyophilized overnight

Sources & evidence

ORD record
ord-8c1bfddc25724283a65a40414d6bc26c
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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