Sodium hydride → HCID 11657009, compound

HRID 862470Notes

Reaction equation

HRID 862470 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8](=[C:18]3[CH2:23][CH2:22][N:21]([C:24]([NH:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:25])[CH2:20][CH2:19]3)[C:9]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:10]=3[CH2:11][CH2:12][C:3]=12.[CH:33]1[CH:34]=[CH:35][C:36]2[N:41]([OH:42])[N:40]=[N:39][C:37]=2[CH:38]=1.[H-].[Na+]>CN(C=O)C>[N:41]1([O:42][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[C:8](=[C:18]4[CH2:23][CH2:22][N:21]([C:24]([NH:26][C:27]5[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=5)=[O:25])[CH2:20][CH2:19]4)[C:9]4[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:10]=4[CH2:11][CH2:12][C:3]=23)[C:36]2[CH:35]=[CH:34][CH:33]=[CH:38][C:37]=2[N:39]=[N:40]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 757711-HydroxybenzotriazoleHCID 11655652HCID 11655652, compound

Product 1

HCID 11657009HCID 11657009, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the title compound from Example 261 (1.0 grams) in dry DMF (60 mL) was added HOBT (1.4 grams), sodium hydride (0.2 grams, 60% in mineral oil) and distilled water (0.5 mL). The solution was stirred at 25° C. under nitrogen while being irradiated with a 200 Watt lamp for 20 hours. The reaction mixture was concentrated in vacuo, diluted with CH2Cl2 and saturated aqueous sodium bicarbonate and after two hours, the organic phase was separated, dried over MgSO4 and concentrated. Purification by flash column chromatography (silica gel) using 3-5% MeOH--CH2Cl2 afforded the title compound (Yield 1.1 grams, 87%, MH+564).

Workup

  1. distillationdistilled water (0.5 mL)
  2. customwhile being irradiated with a 200 Watt lamp for 20 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with CH2Cl2 and saturated aqueous sodium bicarbonate and after two hours
  5. customthe organic phase was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-7afa06c1d3ba46ffaa996b707c7bccfb
Source dataset
uspto-grants-1998_02
Patent number
US05719148

Reaction notes

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