2-Methylpropylenediamine → HCID 178428470, compound

HRID 2421905Notes

Reaction equation

HRID 2421905 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.[NH2:26][CH2:27][C:28](N)([CH3:30])[CH3:29].[S]>C1(C)C=CC=CC=1>[CH3:29][C:28]1([CH3:30])[CH2:27][NH:26][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]1

Participants

5

Reactant 3

HCID 131282-MethylpropylenediamineHCID 5362487SulfurHCID 57896658HCID 57896658, compound

Product 1

HCID 178428470HCID 178428470, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile (30 mg, 0.081 mmol) in toluene (2 mL) was added 1,2-diamino-2-methylpropane (200 μL, 1.908 mmol) and sulfur (20.84 mg, 0.081 mmol). The reaction was heated to 95° C. and stirred at that temperature for 2 h. The reaction mixture was load directly onto a silica gel column and was purified by flash column chromatography using a gradient elution of hexanes with 20-100% EtOAc to provide 7-(4,4-dimethyl-4,5-dihydro-1H-imidazol-2-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (12 mg, 0.026 mmol, 31.9% yield) as an off white solid. LCMS (+ESI) m/z=441.1 [M+H]+; 1H-NMR (CDCl3) δ 8.54 (d, 1H), 8.50 (d, 1H), 7.81 (d, 2H), 7.76 (d, 2H), 3.94 (dd, 2H), 3.87 (dd, 2H), 3.57 (br s, 2H), 1.37 (s, 6H).

Workup

  1. customwas purified by flash column chromatography
  2. washa gradient elution of hexanes with 20-100% EtOAc

Sources & evidence

ORD record
ord-5f16dfe7af6d448381a71611d4a4f024
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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