Dimethylamine → HCID 178433349, compound

HRID 1917518Notes

Reaction equation

HRID 1917518 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:28])[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[Br:27])[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.[CH3:29][NH:30][CH3:31]>C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([CH3:28])[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[Br:27])[NH:10]/[C:11]/2=[N:12]\[O:13][CH:14]([CH2:18][CH2:17][OH:16])[C:15]([N:30]([CH3:31])[CH3:29])=[O:19])[N:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178433342HCID 178433342, compound

Product 1

HCID 178433349HCID 178433349, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)dihydrofuran-2(3H)-one (310 mg, 0.668 mg) in THF (2 mL) was added N,N-dimethylamine (2.0M solution in MeOH, 0.86 mL, 1.72 mmol) and the reaction mixture was stirred overnight at r.t. The solvent was removed and purified by LCMS to afford the title compound 2-((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)-4-hydroxy-N,N-dimethylbutanamide (89, 80 mg, 24%) as white solid. 1H NMR (400 MHz, METHANOL-d4) 62.63 (d, J=2.78 Hz, 3H) 2.84-2.99 (m, 1H) 3.01 (d, J=3.28 Hz, 3H) 3.08-3.25 (m, 4H) 3.61-3.93 (m, 2H) 4.99 (dddd, J=15.03, 4.86, 2.59, 2.27 Hz, 1H) 5.09-5.23 (m, 3H) 5.91 (d, J=9.09 Hz, 1H) 6.98-7.14 (m, 1H) 7.33 (ddd, J=7.89, 4.99, 2.53 Hz, 1H) 7.38-7.48 (m, 1H). MS (ES) [M+H] calculated for C20H25BrFN6O3, 495.34; found 495.30.

Workup

  1. customThe solvent was removed
  2. custompurified by LCMS

Sources & evidence

ORD record
ord-c1b3f103475d41908ef862f2be34fb17
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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