Hydrochloric Acid → HCID 69297453, compound

HRID 1930424Notes

Reaction equation

HRID 1930424 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])[N:7]([CH3:35])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37].Cl.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:37][CH3:36])[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:34])=[O:12])[N:7]([CH3:35])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6364545Methylamine hydrochlorideHCID 69297552HCID 69297552, compound

Product 1

HCID 69297453HCID 69297453, compoundYield 26%

Procedure

Using a procedure analogous to Example A1, 1-(3-t-butyl-1-methyl-1H-pyrazol-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, 0.363 mmol) and MeNH2.HCl (0.0502 g, 0.743 mmol, 2.00 eq) were combined to afford 1-(3-t-butyl-1-methyl-1H-pyrazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.0451 g, 24% yield) as the HCl salt. 1H NMR (400 MHz, DMSO-d6): δ 9.49 (brs, 1H), 9.07 (s, 1H), 8.44-8.41 (m, 1H), 7.97 (brs, 1H), 7.92 (s, 1H), 7.33-7.27 (m, 2H), 6.23 (s, 1H), 3.71 (s, 3H), 3.63 (brs, 3H), 2.94 (s, 3H), 1.24 (s, 9H); MS (ESI) m/z: 479.2 (M+H+).

Sources & evidence

ORD record
ord-33a4861985054f979b5d20f6e209c9b0
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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