L-Alaninol → HCID 68379864, compound

HRID 2178705Notes

Reaction equation

HRID 2178705 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:16](=[O:17])[N:15]3[C:10]([C:11](=[O:18])[O:12][CH2:13][CH2:14]3)=[CH:9][CH:8]=2)[CH:6]=1.[NH2:19][C@@H:20]([CH3:23])[CH2:21][OH:22]>C(#N)C>[OH:12][CH2:13][CH2:14][N:15]1[C:16](=[O:17])[C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[CH:8][CH:9]=[C:10]1[C:11]([NH:19][C@@H:20]([CH3:23])[CH2:21][OH:22])=[O:18]

Participants

4

Reactant 2

HCID 80307L-AlaninolHCID 683801743,4-Dihydro-7-(4-methyl-1H-imidazol-1-yl)pyrido[2,1-c][1,4]oxazine-1,6-dione

Product 1

HCID 68379864HCID 68379864, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 7-(4-methyl-1H-imidazol-1-yl)-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,6-dione (P14) (1.440 g, 5.872 mmol) and (2S)-2-aminopropan-1-ol (1.714 g, 22.82 mmol) in acetonitrile (3 mL) was heated to 85° C. for 20 minutes. The reaction mixture was then allowed to cool to room temperature and diluted with additional acetonitrile (10 mL). Filtration and rinsing with acetonitrile (10 mL) afforded the product as a white solid. Yield: 1.62 g, 5.06 mmol, 86%. 1H NMR (400 MHz, DMSO-d6) δ 1.11 (d, J=6.8 Hz, 3H), 2.14 (d, J=0.9 Hz, 3H), 3.33-3.46 (m, 2H), 3.59-3.66 (m, 2H), 3.89-4.01 (m, 1H), 4.18-4.29 (m, 2H), 4.80 (t, J=5.8 Hz, 1H), 4.94 (t, J=5.4 Hz, 1H), 6.45 (d, J=7.5 Hz, 1H), 7.32-7.34 (m, 1H), 7.69 (d, J=7.5 Hz, 1H), 8.13 (d, J=1.3 Hz, 1H), 8.67 (br d, J=8.3 Hz, 1H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationFiltration
  3. washrinsing with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-ecdd224fb75640bf892e03280c6d0173
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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