Methylamine → HCID 24810934, compound

HRID 599341Notes

Reaction equation

HRID 599341 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:29][C:28]4[C:23](=[N:24][C:25](SC)=[N:26][CH:27]=4)[N:22]([CH3:32])[C:21]3=[O:33])[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[N:42]=[CH:41][CH:40]=[CH:39]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:57][NH2:58]>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:29][C:28]4[C:23](=[N:24][C:25]([NH:58][CH3:57])=[N:26][CH:27]=4)[N:22]([CH3:32])[C:21]3=[O:33])[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[N:42]=[CH:41][CH:40]=[CH:39]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 67063028HCID 67063028, compound

Product 1

HCID 24810934HCID 24810934, compound

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-(3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-methyl-5-(1-methyl-7-(methylamino)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)urea. 1H NMR (400 MHz, DMSO-d6): δ 8.95 (m, 2H), 8.48 (m, 1H); 8.15 (m, 1H), 8.04 (d, J=8 Hz, 1H), 7.92 (m, 2H), 7.60 (dd, J=8, Hz, 1H), 7.17 (d, J=12 Hz, 1H), 7.02 (m, 1H), 6.46 (s, 1H), 4.53 (d, J=14 Hz, 1H), 4.33 (d, J=14 Hz, 1H), 3.25 brs, 3H), 2.78 (d, J=5 Hz, 3H), 2.04 (s, 3H), 1.28 (s, 9H); MS (ESI) m/z 609.2 (M+H+).

Sources & evidence

ORD record
ord-ee47a568b0114394b9b35d4909a4e5ef
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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