2,2-Dimethyl-1,3-propanediamine → HCID 57896774, compound

HRID 2421906Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[N:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:13]2=3)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:26][C:27]([CH3:32])([CH2:30]N)[CH2:28][NH2:29].[S]>CCO>[CH3:26][C:27]1([CH3:32])[CH2:28][NH:29][C:22]([C:20]2[CH:19]=[N:18][C:14]3[O:15][CH2:16][CH2:17][N:12]([S:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:24])([F:1])[F:25])=[CH:4][CH:5]=4)(=[O:10])=[O:11])[C:13]=3[CH:21]=2)=[N:23][CH2:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile (30 mg, 0.081 mmol) in EtOH (2 mL) was added 2,2-dimethylpropane-1,3-diamine (41.5 mg, 0.406 mmol) and sulfur (41.7 mg, 0.162 mmol). The reaction was heated to 80° C. and stirred at that temperature for 6 h. LCMS analysis identified the product as the predominant component of the reaction mixture. The reaction mixture was concentrated in vacuo and the resulting paste was purified by flash column chromatography using a gradient elution of hexanes with 20-100% EtOAc to provide 7-(5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (18.7 mg, 0.039 mmol, 48.1% yield) as an off white solid. LCMS (+ESI) m/z=455.1 [M+H]+; 1H-NMR (CD3OD) δ 8.51 (d, 1H), 8.26 (d, 1H), 8.01 (d, 2H), 7.90 (d, 2H), 3.98 (s, 4H), 3.15 (s, 4H), 1.05 (s, 6H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe resulting paste was purified by flash column chromatography
washa gradient elution of hexanes with 20-100% EtOAc

Sources & evidence

ORD record: ord-42a151f1538b43008d3e8fd51a3bd9fb
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960377B2

Reaction notes

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