1-Phenethylamine, (-)- → HCID 69094410, compound

HRID 1930451Notes

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:32](=[O:33])[N:31]([CH3:34])[C:23]4[N:24]=[C:25](S(C)=O)[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:35])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][C@H:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[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:32](=[O:33])[N:31]([CH3:34])[C:23]4[N:24]=[C:25]([NH:44][C@H:37]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH3:36])[N:26]=[CH:27][C:22]=4[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:35])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 758181-Phenethylamine, (-)-

HCID 69040323HCID 69040323, compound

Product 1

HCID 69094410HCID 69094410, compoundYield 30%

Procedure

Using a procedure analogous to Example 57, 1-(3-t-butylisoxazol-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 43 (0.150 g, 0.311 mmol, 1.00 eq) and L-(−)-alpha-methylbenzylamine (0.0846 ml, 0.656 mmol, 3.00 eq) were combined to afford (S)-1-(3-tert-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-methyl-7-oxo-2-(1-phenylethylamino)-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (36 mg, 30% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.34 (s, 1H), 8.73 (brs, 1H), 8.65 (brs, 1H), 8.51 (d, J=7.6 Hz, 1H), 8.37 (d, J=7.6 Hz, 1H), 7.85 (s, 1H), 7.44-7.38 (m, 2H), 7.31-7.25 (m, 4H), 7.20-7.16 (m, 1H), 6.06 (s, 1H), 5.16-5.09 (m, 1H), 3.48 (s, 3H), 1.48 (d, J=7.2 Hz, 3H), 1.23 (s, 9H); MS (ESI) m/z: 556.3(M+H+).

Sources & evidence

ORD record: ord-abfda959174b4cc693d6941ce6c2a5e2
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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