Sodium borohydride → HCID 178512258, compound

HRID 1532763Notes

Reaction equation

HRID 1532763 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25])=[N:15][C:16]#[N:17])C=C.[BH4-].[Na+].CO.C(Cl)(Cl)Cl>C1COCC1>[OH:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25])=[N:15][C:16]#[N:17]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21584188Chloroform methanolHCID 178458510HCID 178458510, compound

Product 1

HCID 178512258HCID 178512258, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(2-Allyloxy-4-cyanophenyl)-N′-(2-bromophenyl)-N″-cyanoguanidine (100 mg, 0.25 mmol) and sodium borohydride (20 mg, 0.52 mmol) in THF (3 ml) was added at rt tetrakistriphenylphosphine palladium[0] (21 mg, 7 mol %). The reaction was stirred at rt until tlc showed no starting material present. The mixture was partitioned between ethyl acetate and 0.5 M sodium dihydrogen phosphate. After drying over MgSO4 filtration and evaporation under reduced pressure afforded a crude tan solid (100 mg). Column chromatography on silica gel eluting with 5% methanol/chloroform gave the title compound as a pale yellow solid (64 mg) which was recrystallized from chloroform (42 mg, 47%). 1H NMR(400 MHz,DMSO) δ 10.93 (s, 1H), 9.57 (s, 1H), 8.74(s, 1H), 7.84 (d, J=8.3 Hz, 1H),7.71 (d, J=7.8 Hz, 2H), 7-50-7.42 (m, 2H), 7-30-7.26 (m, 2H 7.17 (s, 1H), 7.08 (t, 1H); IR(KBr) 2224,2193 cm−1; MS(ES−) m/e 354,356 [M−H]−; MS(ES+) m/e 356,358 [M+H]+; mp. 175-176°.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 0.5 M sodium dihydrogen phosphate
  2. dry with materialAfter drying over MgSO4 filtration and evaporation under reduced pressure
  3. customafforded a crude tan solid (100 mg)

Sources & evidence

ORD record
ord-f35f2b867489479b81e97553c96960b1
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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