N-methyl-2-pyrrolidone → 2-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide

HRID 1054918Notes

Reaction equation

HRID 1054918 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[CH:16]=[CH:17][C:18]([NH2:20])=[N:19][C:11]2=3)(=[O:9])=[O:8])[CH:2]=1.CN(C(ON1N=N[C:32]2[CH:33]=[CH:34][CH:35]=N[C:31]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:46](N(C(C)C)CC)([CH3:48])[CH3:47].CN1CCC[C:57]1=[O:61]>>[C:33]1([CH:32]([CH3:31])[C:57]([NH:20][C:18]2[CH:17]=[CH:16][C:12]3[O:13][CH2:14][CH2:15][N:10]([S:7]([C:3]4[CH:2]=[C:1]([CH3:21])[CH:6]=[CH:5][CH:4]=4)(=[O:9])=[O:8])[C:11]=3[N:19]=2)=[O:61])[CH:34]=[CH:35][CH:48]=[CH:46][CH:47]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1180617154-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine

Product 1

HCID 725442142-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide

Procedure

4-(Toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine (20 mg, 0.065 mmol) was dissolved in N-methylpyrrolidinone (0.5 mL), followed by (d,l)-2-phenylpropionic acid (30 μL, 0.11 mmol), HATU (45 mg, 0.12 mmol), and diisopropyl ethylamine (23 μL, 0.13 mmol). The reaction mixture was stirred at room temperature for 18 hours. Then, the reaction mixture was then purified by HPLC to give 2-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide. LCMS (ESI): calc. C23H23N3O4S=437; obs. M+H=438.

Workup

  1. customThen, the reaction mixture was then purified by HPLC

Sources & evidence

ORD record
ord-f03919e9bec84b98808144c981959c4d
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

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