N,N-Dimethylethylenediamine → HCID 69036662, compound

HRID 1930427Notes

Reaction equation

HRID 1930427 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]([NH:28][CH3:29])[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][N:37]([CH3:41])[CH2:38]CN>>[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:28][CH2:29][CH2:36][N:37]([CH3:41])[CH3:38])[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])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 69297453HCID 69297453, compound

Product 1

HCID 69036662HCID 69036662, compound

Procedure

Using general method E, 1-(3-t-butyl-1-methyl-1H-pyrazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 12 (0.199 g, 0.389 mmol) and N1,N1-dimethylethane-1,2-diamine (0.214 ml, 1.94 mmol, 5.00 eq) were combined to afford 1-(3-t-butyl-1-methyl-1H-pyrazol-5-yl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)urea which was subsequently treated with HCl to afford hydrochloride salt (20.8 mg, 10% yield) as a white solid. 1H NMR (400 MHz, DMSO-d4): δ 9.07 (s, 1H), 8.91 (brs, 1H), 8.80-8.75 (brs, 1H), 8.47-8.44 (m, 1H), 8.01 (brs, 1H), 7.97 (s, 1H), 7.33-7.27 (m, 2H), 6.10 (s, 1H), 3.77-3.72 (m, 2H), 3.63 (s, 3H), 3.51 (brs, 3H), 3.37-3.33 (brm, 2H), 2.86 (m, 6H), 1.21 (s, 9H); MS (ESI) m/z: 536.2 (M+H+).

Sources & evidence

ORD record
ord-bb9dc0351a474dcc87c81c968bb20dca
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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