Hydrogen Bromide → 5-(azetidin-3-ylamino)-2'-(methylamino)-[3,4'-bipyridin]-6(1H)-one di-hydrobromide

HRID 2283469Notes

Reaction equation

HRID 2283469 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH3:16])[CH:10]=2)=[CH:5][C:4]=1[NH:17][CH:18]1[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]1.CO.[BrH:31]>>[BrH:31].[BrH:31].[NH:20]1[CH2:21][CH:18]([NH:17][C:4]2[C:3](=[O:2])[NH:8][CH:7]=[C:6]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH3:16])[CH:10]=3)[CH:5]=2)[CH2:19]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 887MethanolHCID 118251491Tert-butyl 3-((6-methoxy-2'-(methylamino)-[3,4'-bipyridin]-5-yl)amino)azetidine-1-carboxylate

Product 1

HCID 1182509885-(azetidin-3-ylamino)-2'-(methylamino)-[3,4'-bipyridin]-6(1H)-one di-hydrobromideYield 89%

Procedure

A solution of tert-butyl 3-((6-methoxy-2′-(methylamino)-[3,4′-bipyridin]-5-yl)amino)azetidine-1-carboxylate (890 mg, 2.31 mmol) in 40% HBr (9 mL) was stirred at 50° C. for 14 h. After the mixture was cooled to RT, 9 mL of methanol was added, the residue filtered, washed with ethyl acetate (5 mL), and dried in vacuo to afford 5-(azetidin-3-ylamino)-2′-(methylamino)-[3,4′-bipyridin]-6(1H)-one di-hydrobromide (947 mg, 89%) as yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 12.97 (s, 1H), 12.18 (d, J=5.9 Hz, 1H), 8.87 (s, 1H), 8.68 (s, 1H), 8.50 (s, 1H), 7.89 (d, J=6.8 Hz, 1H), 7.52 (dd, J=5.8, 2.6 Hz, 1H), 7.23 (s, 1H), 7.20 (dd, J=7.0, 1.8 Hz, 1H), 6.60 (s, 1H), 6.50 (d, J=2.5 Hz, 1H), 4.48 (d, J=8.9 Hz, 1H), 4.34 (m, 2H), 4.09-3.97 (m, 2H), 2.99 (d, J=4.8 Hz, 3H); MS (ES) m/z 272 (M+H).

Workup

  1. filtrationthe residue filtered
  2. washwashed with ethyl acetate (5 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-41c34bf6c7954e95aa447a5e41610746
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

Loading…