Sodium borohydride → HCID 22046379, compound

HRID 1830770Notes

Reaction equation

HRID 1830770 reaction equation
[C:1]([C:9]1[N:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[O:17])=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[O:17])=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22046279HCID 22046279, compound

Product 1

HCID 22046379HCID 22046379, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(5-benzoyl-pyrazin-2-yl)-3-(2-methoxy-5-methyl-phenyl)-urea (22 mg; 0.061 mmol) in methanol (1 mL) was added sodium borohydride (10 mg; 0.3 mmol). After stirring for 12 hours, the reaction diluted with 30 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×30 mL), brine (30 mL), then dried (MgSO4), and filtered. The filtered material was concentrated under reduced pressure to yield a white solid (91% yield). 1H NMR (400 MHz, CDCl3) δ8.48 (br s, 1H), 8.39 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 7.25-7.45 (m, 5H), 6.89 (d, 1H), 6.80 (d, 1H), 5.85 (d, 1H), 3.88 (s, 3H), 2.37 (s, 3H). LRMS (ESI, Positive) m/e 365.24 (M+1).

Workup

  1. washwashed with aqueous 10% sodium carbonate (1×30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered material was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f47c9b093e147de8bba9b78e222bd86
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

Loading…