Ammonia methanol → HCID 178489728, compound

HRID 656619Notes

Reaction equation

HRID 656619 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:35])[C:5]2=[C:6]([CH2:8][C@H:9]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[N:28]=3)[NH:10]/[C:11]/2=[N:12]\[O:13][CH:14]2[CH2:18][CH2:17][O:16][C:15]2=[O:19])[N:7]=1.[NH3:36].CO>>[NH2:1][C:2]1[N:3]=[C:4]([CH3:35])[C:5]2=[C:6]([CH2:8][C@H:9]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[N:28]=3)[NH:10]/[C:11]/2=[N:12]\[O:13][CH:14]([CH2:18][CH2:17][OH:16])[C:15]([NH2:36])=[O:19])[N:7]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 178489723HCID 178489723, compound

Product 1

HCID 178489728HCID 178489728, compoundYield 89%

Procedure

3-((Z)—((R)-2-amino-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)dihydrofuran-2(3H)one (14.3 mg, 0.03 mmol) was dissolved in 7N NH3-MeOH solution and stirred overnight in a sealed tube. The solvent was removed and residue dried to afford the title compound 2-((Z)—((R)-2-amino-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)-4-hydroxybutanamide (13.2 mg, 89%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ 1.83-2.16 (m, 2H) 2.58 (d, J=6.06 Hz, 3H) 2.85-3.03 (m, 1H) 3.07-3.25 (m, 1H) 3.70 (q, J=7.24 Hz, 2H) 3.90 (d, J=11.37 Hz, 3H) 4.54 (td, J=7.83, 5.05 Hz, 1H) 4.97-5.17 (m, 1H) 6.69-6.85 (m, 1H) 7.11 (dd, J=7.71, 2.40 Hz, 1H) 7.14-7.26 (m, 2H) 7.57-7.72 (m, 1H) 7.76 (dd, J=15.03, 6.69 Hz, 1H). MS (ES) [M+H] calculated for C24H27FN7O4, 496.50. found 496.40.

Workup

  1. customThe solvent was removed
  2. customresidue dried

Sources & evidence

ORD record
ord-e5bad231e20c438382161517c274bcc9
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

Loading…