Acetic Acid → HCID 89934139, compound

HRID 921958Notes

Reaction equation

HRID 921958 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([Cl:31])=[C:10]([NH:16][C:17]3[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]4=[N:26][CH:27]=[C:28]([C:29]#[N:30])[N:19]4[N:18]=3)[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=2)[CH2:4][C@H:3]1[OH:32].[CH:33](OC)(OC)[O:34]C.CC(O)=O.[O:44]1[CH2:47][C:46](=O)[CH2:45]1>CO.CN(C=O)C>[Cl:31][C:9]1[C:8]([N:5]2[CH2:6][CH2:7][C@H:2]3[N:1]([CH:46]4[CH2:45][O:44][CH2:47]4)[C:33](=[O:34])[O:32][C@@H:3]3[CH2:4]2)=[CH:13][C:12]([C:14]#[N:15])=[CH:11][C:10]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]2=[N:26][CH:27]=[C:28]([C:29]#[N:30])[N:19]2[N:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 150242543-OxetanoneHCID 86708622HCID 86708622, compound

Product 1

HCID 89934139HCID 89934139, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

(+/−)-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 (80 mg, 0.177 mmol) was taken up in MeOH (1.0 mL) and DMF (1.0 mL) and trimethyl orthoformate (1.464 mL, 13.25 mmol), AcOH (0.040 mL, 0.707 mmol), and oxetan-3-one (0.113 mL, 1.766 mmol) were added. The reaction was stirred at room temperature for 2 h, then NaCNBII3 (111 mg, 1.766 mmol) was added and the reaction stirred at 25° C. overnight.

Workup

  1. stirringthe reaction stirred at 25° C. overnight

Sources & evidence

ORD record
ord-1525acee2b784d5793c18776379158ef
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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