Dimethylamine → HCID 178433349, compound

HRID 656620Notes

Reaction equation

HRID 656620 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) δ 2.63 (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-586365ec79c642779f57561ba099a41e
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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