2-Fluoropyridine → HCID 178420493, compound

HRID 1846800Notes

Reaction equation

HRID 1846800 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([NH2:20])[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([NH:20][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 97462-FluoropyridineHCID 178511713HCID 178511713, compound

Product 1

HCID 178420493HCID 178420493, compound

Conditions

Temperature
160 °C

Procedure

trans-4-(3-(Tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexanamine (0.053 g, 0.19 mmol) and 2-fluoropyridine (0.033 mL, 0.38 mmol) were mixed in a microwave tube. The tube was sealed, and the mixture was stirred neat at 160° C. for 3 d. The crude mixture was purified via silica gel column chromatography to give N-(trans-4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexyl)pyridin-2-amine as a brown solid. [M+1] 355.2. IC50 (uM): 2.665.

Workup

  1. customThe tube was sealed
  2. customThe crude mixture was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-186e74f9a5d649a28fb261db61bb5318
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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