Methylamine → HCID 24811039, compound

HRID 599345Notes

Reaction equation

HRID 599345 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13](SC)=[N:14][CH:15]=3)[N:10]([CH2:20][CH3:21])[C:9]2=[O:22])=[CH:6][C:5]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:25])=[C:4]([F:37])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:49][NH2:50]>>[Cl:1][C:2]1[C:7]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([NH:50][CH3:49])=[N:14][CH:15]=3)[N:10]([CH2:20][CH3:21])[C:9]2=[O:22])=[CH:6][C:5]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:25])=[C:4]([F:37])[CH:3]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 67063180HCID 67063180, compound

Product 1

HCID 24811039HCID 24811039, compoundYield 88%

Procedure

Using a procedure analogous to Example A2, the sulfide was oxidized with mCPBA to the sulfone and then treated with methylamine to provide 1-(4-chloro-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-2-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)urea (0.279 mmol, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.51 (s, 1H), 8.32 (d, J=8.0 Hz, 1H), 8.06 (s, 1H), 7.96 (brs, 1H), 7.87 (s, 1H), 7.64 (d, J=11 Hz, 1H), 7.50 (m, 2H), 7.33 (m, 1H), 7.02 (m, 1H), 4.60 (d, J=14 Hz, 1H), 4.40 (d, J=14 Hz, 1H), 3.95 (m, 2H), 2.78 (d, J=5 Hz, 3H), 1.15 (t, 3H); MS (ESI) m/z: 538.3 (M+H+).

Sources & evidence

ORD record
ord-37f3f6c1fa724d2db478c17be2d5bd95
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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