Sodium dicyanamide → HCID 131719589, compound

HRID 864095Notes

Reaction equation

HRID 864095 reaction equation
O[NH:2][N:3]=[CH:4][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13](=[O:34])[C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19](=[O:33])[C@@H:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:7][CH2:6]1.[N-:35](C#N)[C:36]#N.[Na+]>CCCCO>[C:36]([NH:2][N:3]=[CH:4][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13](=[O:34])[C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19](=[O:33])[C@@H:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:7][CH2:6]1)#[N:35]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 67768813HCID 67768813, compound

Product 1

HCID 131719589HCID 131719589, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred solution of Example 3 Part D compound (220 mg, 0.40 mmol) in 3.0 mL of n-BuOH was added sodium dicyanamide (99.0 mg, 1.00 mmol). The reaction mixture was heated to reflux for 14 h and concentrated in vacuo. This was purified by preparative HPLC to give 124 mg (57%) of title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. concentrationconcentrated in vacuo
  4. customThis was purified by preparative HPLC

Sources & evidence

ORD record
ord-adcbe45d1c3e4a778b6055fb9200d9e0
Source dataset
uspto-grants-1996_10
Patent number
US05561146

Reaction notes

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