Sodium borohydride → HCID 10028781, compound

HRID 1725351Notes

Reaction equation

HRID 1725351 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:23])[CH2:4][N:5]1[CH2:9][C@@H:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[N:18]=3)[N:13]=[CH:12][CH:11]=2)[O:7][C:6]1=[O:22].[O:24]=[C:25]1[CH2:30][S:29][C:28]2[CH:31]=[CH:32][C:33]([CH:35]=O)=[N:34][C:27]=2[NH:26]1.[BH4-].[Na+]>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[OH:23][C@H:3]([CH2:4][N:5]1[CH2:9][C@@H:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[N:18]=3)[N:13]=[CH:12][CH:11]=2)[O:7][C:6]1=[O:22])[CH2:2][NH:1][CH2:35][C:33]1[CH:32]=[CH:31][C:28]2[S:29][CH2:30][C:25](=[O:24])[NH:26][C:27]=2[N:34]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 68839620HCID 68839620, compound

Product 1

HCID 10028781HCID 10028781, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To (R)-3-((S)-3-Amino-2-hydroxy-propyl)-5-(6-methoxy-[1,5]naphthyridin-4-yl)-oxazolidin-2-one (0.069 g, 0.22 mmol) in CH2Cl2 (7 mL) and MeOH (1.8 mL) was added 3-oxo-3,4-dihydro-2H-pyrido[3,2,b][1,4]thiazine-6-carbaldehyde (SB-735214, 0.043 g, 0.22 mmol) and the reaction mixture was stirred for 15 hours. Sodium borohydride (0.01 g, 0.26 mmol) was added followed by methanol (5 mL). After 1 hour, the reaction mixture was diluted with chloroform and washed with saturated aqueous NaHCO3 solution, dried (MgSO4), filtered and concentrated. Flash chromatography on silica gel using a gradient of 0-10% MeOH/CHCl3 afforded the product as a white solid (0.082 g, 76%) 1H NMR (400 MHz, CDCl3): δ8.80 (d, J=4.6 Hz, 1H); 8.25 (d, J=9.1 Hz, 1H); 7.70 (d, J=4.4 Hz, 1H); 7.55 (d, J=7.6 Hz, 1H); 7.16 (d, J=9.1 Hz, 1H); 6.87 (d, J=7.9 Hz, 1H); 6.32 (dd, J=8.7, 7.2 Hz, 1H); 4.57 (t, J=9.4 Hz, 1H); 4.04 (s, 3H); 3.91 (m, 1H); 3.75-3.84 (overlapping signals, 2H); 3.63 (dd, J=9.2, 6.9 Hz, 1H); 3.47-3.50 (overlapping signals, 2H); 3.46 (s, 2H); 3.22 (dd, J=14.4, 6.8 Hz, 1H); 2.79 (dd, J=12.4, 3.6 Hz, 1H); 2.57 (dd, J=12.4, 8.3 Hz, 1H). MS (ES) m/e 497 (M+H)+.

Workup

  1. waitAfter 1 hour
  2. washwashed with saturated aqueous NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e209aadef3af4dcb9c91de4a82223709
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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