Methylamine → N-[4-methyl-3-(8-methyl-2-methylamino-7-oxo-7,8-dihydropteridin-6-yl)-phenyl]-3-trifluoromethyl-benzamide

HRID 29822Notes

Reaction equation

HRID 29822 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[C:21]1[C:30](=[O:31])[N:29]([CH3:32])[C:28]2[N:27]=[C:26](Cl)[N:25]=[CH:24][C:23]=2[N:22]=1.[CH3:34][NH2:35].C1COCC1>CS(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[C:21]1[C:30](=[O:31])[N:29]([CH3:32])[C:28]2[N:27]=[C:26]([NH:35][CH3:34])[N:25]=[CH:24][C:23]=2[N:22]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 59723641HCID 59723641, compound

Product 1

HCID 11532864N-[4-methyl-3-(8-methyl-2-methylamino-7-oxo-7,8-dihydropteridin-6-yl)-phenyl]-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A Smith vial (2-5 mL) is charged with N-[4-methyl-3-(2-chloro-8-methyl-7-oxo-7,8-dihydropteridin-6-yl)-pheny]-3-trifluoromethyl-benzamide (15 mg, 0.032 mmol), 2M methylamine solution in THF (160 μL, 0.32 mmol), and DMSO (0.5 mL). After purging with Argon, the vial is sealed and irradiated at 100° C. for 45 minutes in a Smith Synthesizer. The resulting solution is subjected to purification by reverse-phase LC-MS to yield the title compound; 1H NMR 400 MHz (DMSO-d6) δ 10.51 (s, 1H), 8.68 (s, 1H), 8.31 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 8.02 (bs, 1H), 7.96 (d, J=7.2 Hz, 1H), 7.80-7.76 (m, 3H), 7.27 (d, J=8.2 Hz, 1H), 3.56 (s, 3H), 2.94 (s, 3H), 2.19 (s, 3H); MS m/z 469.3 (M+1).

Workup

  1. customAfter purging with Argon
  2. customthe vial is sealed
  3. customirradiated at 100° C. for 45 minutes in a Smith Synthesizer
  4. customThe resulting solution is subjected to purification by reverse-phase LC-MS

Sources & evidence

ORD record
ord-9ba0f03d61a140808e09cfdb264dcbc2
Source dataset
uspto-grants-2008_09
Patent number
US07423038B2

Reaction notes

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