Hydrochloric Acid → HCID 67294242, compound

HRID 517939Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:36][CH3:37])=[CH:4][C:5]([C:10]2[CH:31]=[CH:30][C:13]([O:14][CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[C:12]([C:32]([F:35])([F:34])[F:33])[CH:11]=2)=[N:6][C:7]=1[C:8]#[N:9].Cl.[N:39]([O-])=O.[Na+].C(OCC)(=O)C>CN1C(=O)CCC1.O>[C:8]([C:7]1[C:2]2[N:1]=[N:39][N:36]([CH3:37])[C:3]=2[CH:4]=[C:5]([C:10]2[CH:31]=[CH:30][C:13]([O:14][CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[C:12]([C:32]([F:35])([F:33])[F:34])[CH:11]=2)[N:6]=1)#[N:9]

Participants

Conditions

Temperature: 7.5 °C

Procedure

To tert-butyl 4-(2-(4-(5-amino-6-cyano-4-(methylamino)pyridin-2-yl)-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate (1.8 g) in NMP (20 ml) was added 1M hydrochloric acid (15 ml) and cooled to 5-10° C. with an ice bath. To above solution was then added dropwise a solution of sodium nitrite (0.335 g) in water (3 ml) during 2 minutes. The mixture was stirred further at room temperature for another 1 hour. After adding ethyl acetate (200 ml), the mixture washed with water (4×100 ml), brine (50 ml), solvent removed under reduced pressure and residue was columned on silica gel using 2:1 EtOAc:Heptane as eluant to give tert-butyl 4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-piperidine-1-carboxylate (1.55 g) as a white solid.

Workup

washthe mixture washed with water (4×100 ml), brine (50 ml), solvent
customremoved under reduced pressure and residue

Sources & evidence

ORD record: ord-326a7dadf8fc47b889901fbbe62a2580
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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