N,N-Dimethylethylenediamine → HCID 68982139, compound

HRID 1930440Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26](SC)[N:27]=[CH:28][C:23]=4[CH:22]=3)[CH:18]=[CH:17][C:16]=2[F:35])=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37]([CH3:41])[CH2:38][CH2:39][NH2:40]>>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26]([NH:40][CH2:39][CH2:38][N:37]([CH3:41])[CH3:36])[N:27]=[CH:28][C:23]=4[CH:22]=3)[CH:18]=[CH:17][C:16]=2[F:35])=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 66053N,N-Dimethylethylenediamine

HCID 69088835HCID 69088835, compound

Product 1

HCID 68982139HCID 68982139, compoundYield 86%

Procedure

Using a procedure analogous to Example A1, 1-(3-tert-butylphenyl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.200 g, 0.407 mmol) and N,N-dimethylethylenediamine (0.181 mL, 1.65 mmol) were combined to afford 1-(3-tert-butylphenyl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)urea (0.150 g, 86% yield) as a light yellow solid. It was converted to corresponding HCl salt by reacting with HCl (4.0 M HCl in dioxane, 1.0 eq.). 1H NMR (400 MHz, DMSO-d6): δ 9.28 (s, 1H), 8.73 (s, 1H), 8.64 (d, J=1.6 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H), 8.04 (s, 1H), 7.93 (s, 1H), 7.43 (s, 1H), 7.28-7.24 (m, 3H), 7.18 (t, J=8.0 Hz, 1H), 6.99 (tt, J=7.6, 0.8 Hz, 1H), 3.74 (broad, 2H), 3.63 (s, 3H), 3.30 (broad, 2H), 2.81 (d, J=4.8 Hz, 6H), 1.25 (s, 9H); MS (ESI) m/z: 532.3 (M+H+).

Sources & evidence

ORD record: ord-2036067f48e34c0ea40bd9d6999a1725
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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