Hydrochloric Acid → HCID 59536921, compound

HRID 220659Notes

Reaction equation

HRID 220659 reaction equation
[NH2:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10].[O-:19][C:20]#[N:21].[K+].Cl>O.CO>[C:20]([NH:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10])(=[O:19])[NH2:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanate2×HCID 59536931HCID 59536931, compound

Product 1

HCID 59536921HCID 59536921, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

Of the compound from Example 113A, 330 mg (1.15 mmol) in 12 ml of water/methanol 1:1 were admixed at RT with 279 mg (3.44 mmol) of potassium cyanate. The mixture was heated at 40° C. for 1 h and then admixed with 1.15 ml of 1M hydrochloric acid (1.15 mmol) and stirred overnight at RT. A further 93 mg (1.14 mmol) of potassium cyanate were added and the mixture was stirred further at RT for 3 h. The entire reaction mixture was purified by preparative HPLC [Method 10]. The product fraction was freed from the solvents on a rotary evaporator. Drying of the residue in an HV gave 292 mg (80% of theory) of the title compound.

Workup

  1. stirringthe mixture was stirred further at RT for 3 h
  2. customThe entire reaction mixture
  3. customwas purified by preparative HPLC [Method 10]
  4. customThe product fraction was freed from the solvents on a rotary evaporator
  5. customDrying of the residue in an HV

Sources & evidence

ORD record
ord-b9e480b21bfb43bdae532a19b81fc886
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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