m-Chloroperbenzoic acid → HCID 68981913, compound

HRID 1930432Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:34])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:46][NH2:47].Cl>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:47][CH3:46])[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:34])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 70297m-Chloroperbenzoic acid

HCID 6364545Methylamine hydrochloride

HCID 69297847HCID 69297847, compound

Product 1

HCID 68981913HCID 68981913, compoundYield 53%

Procedure

Using a procedure analogous to Example A1, 1-(3-t-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.180 g, 0.373 mmol, 1.00 eq) was oxidized with MCPBA (70.00 wt %, 0.276 g, 1.12 mmol, 3.00 eq) and then subjected to MeNH2.HCl (0.019 g, 0.28 mmol, 2.00 eq) to afford 1-(3-t-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.0346 g, 53% yield) as an off-white solid. The free base thus obtained converted to the hydrochloride (32.3 mg) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.45 (s, 1H), 8.840 (s, 1H), 8.69 (brs, 1H), 8.42 (dd, J=8.0, 2.0 Hz, 1H), 7.92 (s, 1H), 7.90 (brs, 1H), 7.39-7.29 (m, 2H), 6.09 (s, 1H), 3.64 (brs, 3H), 2.93 (brs, 3H), 1.26 (s, 9H); MS (ESI) m/z: 466.2 (M+H+).

Sources & evidence

ORD record: ord-c2bff8c7a66d46f89737960262ed55f1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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