Trifluoroacetic acid → HCID 86708622, compound

HRID 921957Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([Cl:40])=[C:10]([NH:16][C:17]3[N:22]=[C:21]([N:23](CC)[CH2:24][C:25]4C=CC(OC)=CC=4)[C:20]4=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:19]4[N:18]=3)[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=2)[CH2:4][C@H:3]1[OH:41].C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCCl>[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([Cl:40])=[C:10]([NH:16][C:17]3[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]4=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:19]4[N:18]=3)[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=2)[CH2:4][C@H:3]1[OH:41]

Participants

Conditions

Temperature: 25 °C

Procedure

(+/−)-2-((3-((3R,4R)-4-amino-3-hydroxypiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (390 mg, 0.681 mmol) was mixed with anisole (0.372 mL, 3.40 mmol) and DCE (3 mL). TFA (1.049 mL, 13.61 mmol) was added and the mixture was stirred at 25° C. for 1 hr. The mixture was concentrated to dryness under high-vac. 30 ml 2N NH3/MeOH was added and stirred for 30 min. The white precipitate was collected by filtration and washed with 20 ml cold MeOH, ether, and dried under air-suction for 2 hrs to give rac-2-((3-((3R,4R)-4-amino-3-hydroxypiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (193 mg).

Workup

concentrationThe mixture was concentrated to dryness under high-vac
addition30 ml 2N NH3/MeOH was added
stirringstirred for 30 min
filtrationThe white precipitate was collected by filtration
washwashed with 20 ml cold MeOH, ether
customdried under air-suction for 2 hrs

Sources & evidence

ORD record: ord-e824c0261ec74f3b9047578779f3fef3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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