HCID 86681010, compound → HCID 86681011, compound

HRID 1847977Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]3[N:15]=[C:16]([S:18][CH3:19])[S:17][C:13]=3[CH:12]=2)[C:6]([N+:22]([O-])=O)=[CH:5][CH:4]=1>C(O)(=O)C.CCOC(C)=O.[Zn]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]3[N:15]=[C:16]([S:18][CH3:19])[S:17][C:13]=3[CH:12]=2)[C:6]([NH2:22])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 6-methoxy-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine (431 mg, 1.19 mmol) from Step 5 of this Example in acetic acid (6 mL) was added zinc powder (235 mg, 3.57 mmol) slowly at 0° C. The reaction mixture was stirred at 0° C. for 20 min and then stirred at rt for 4 h. The resulting reaction mixture was diluted with 30 mL of EtOAc and filtered through a Celite pad. The filtrate was neutralized with saturated aq NaHCO3. The organic layer was separated, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture of EtOAc-CH2Cl2 (1:3, v/v) as eluent to give 6-methoxy-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine as a brown oil (389 mg, 98%). LCMS (ESI) m/z 333 (M+H)+.

Workup

stirringstirred at rt for 4 h
customThe resulting reaction mixture
filtrationfiltered through a Celite pad
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe crude product was purified on a silica gel column
additiona mixture of EtOAc-CH2Cl2 (1:3

Sources & evidence

ORD record: ord-25185f99227542d39248a31edf5d7984
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

Loading…