Hydrochloric Acid → HCID 117640814, compound

HRID 869985Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]([NH:17][C:18]([C:20]3([C:23]4[CH:33]=[CH:32][C:26]5[O:27][C:28]([F:31])([F:30])[O:29][C:25]=5[CH:24]=4)[CH2:22][CH2:21]3)=[O:19])[N:11]=2)[CH:5]=[N:6][C:7]=1[O:8]C.Cl>O1CCOCC1>[NH2:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:10]2[N:11]=[C:12]([NH:17][C:18]([C:20]3([C:23]4[CH:33]=[CH:32][C:26]5[O:27][C:28]([F:30])([F:31])[O:29][C:25]=5[CH:24]=4)[CH2:21][CH2:22]3)=[O:19])[CH:13]=[CH:14][C:15]=2[CH3:16])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To N-(5′-amino-6′-methoxy-3-methyl-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (53 mg, 0.1166 mmol) in 1,4-dioxane (2 mL) was added 4M aq hydrochloric acid (0.5 mL, 2.0 mmol) and the reaction mixture was heated to 90° C. After one hour the reaction was quenched with triethlyamine (0.5 mL). The reaction mixture was evaporated to dryness and the residue was dissolved in N,N-dimethylformamide (2 mL) and purified by reverse phase HPLC. The fractions from the HPLC purification were neutralized with saturated sodium bicarbonate and extracted with ethyl acetate (3×10 mL). The organics were dried over sodium sulfate and evaporated to yield the product (26 mg, 48%). ESI-MS m/z calc. 440.4. found 441.3 (M+1)+. Retention time 1.39 minutes.

Workup

customAfter one hour the reaction was quenched with triethlyamine (0.5 mL)
customThe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in N,N-dimethylformamide (2 mL)
custompurified by reverse phase HPLC
customThe fractions from the HPLC purification
extractionextracted with ethyl acetate (3×10 mL)
dry with materialThe organics were dried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-50c51252be2841279e574cea4233d367
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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