Hydrochloric Acid → HCID 86655249, compound

HRID 1888008Notes

Reaction equation

HRID 1888008 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19]S(C(C)(C)C)=O)[CH2:18][O:17][CH2:16]3)=[CH:11][CH:10]=2)[C:5]([N+:26]([O-:28])=[O:27])=[CH:4][CH:3]=1.Cl.CCCCCC>C(Cl)Cl.O1CCOCC1>[ClH:1].[NH2:19][C:15]1([C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]3[C:5]([N+:26]([O-:28])=[O:27])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=3)=[CH:14][CH:13]=2)[CH2:16][O:17][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 86655251HCID 86655251, compound

Product 1

HCID 86655249HCID 86655249, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Deprotection/protection step: To a solution of N-(3-{4-[(6-chloro-3-nitropyridin-2-yl)amino]phenyl}oxetan-3-yl)-2-methylpropane-2-sulfinamide (95 mg) in DCM (5 ml) was added dropwise a solution of hydrogen chloride in dioxane (4 M, 111 ul) at room temperature. The reaction mixture was stirred for 10 min. Hexane was added to the suspension and the solid was filtered to give N-[4-(3-aminooxetan-3-yl)phenyl]-6-chloro-3-nitropyridin-2-amine hydrochloride. To a suspension of N-[4-(3-aminooxetan-3-yl)phenyl]-6-chloro-3-nitropyridin-2-amine hydrochloride in THF (3 mL) chilled to 0° C. was added saturated sodium bicarbonate solution (6 mL) and followed by a solution of di-tert-butyl dicarbonate (145 mg) in THF (3 mL) dropwise. After being stirred at room temperature over night, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (59 mg, 2 steps 63%). 400 M Hz 1H-NMR (DMSO-d6) δ: 10.14 (s, 1H), 8.55 (d, J=8.7 Hz, 1H), 8.10 (brs, 1H), 7.62 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 7.01 (d, J=8.7 Hz, 1H), 4.82 (d, J=6.4 Hz, 2H), 4.68 (d, 2H, J=6.4 Hz), 1.50-1.10 (m, 9H); LCMS: 421 [M+H].

Workup

  1. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-e393e179c939456181507886b91ba62a
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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