Methanol → HCID 87099630, compound

HRID 709154Notes

Reaction equation

HRID 709154 reaction equation
[O-:1][C:2]#[N:3].[K+].Cl.[NH2:6][CH:7]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=1[Cl:40])[CH2:8][NH:9][C:10](=[O:32])[CH2:11][N:12]1[C:16](=[O:17])[N:15]([CH2:18][C@H:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[C:14]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:13]1.O.CO>CS(C)=O>[C:2]([NH:6][CH:7]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=1[Cl:40])[CH2:8][NH:9][C:10](=[O:32])[CH2:11][N:12]1[C:16](=[O:17])[N:15]([CH2:18][C@H:19]([OH:24])[C:20]([F:21])([F:23])[F:22])[C:14]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:13]1)(=[O:1])[NH2:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11378442Potassium cyanate2×HCID 89764468HCID 89764468, compound

Product 1

HCID 87099630HCID 87099630, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

12 mg of potassium cyanate (153 μmol) were added to a mixture of 30 mg (51 μmol) of the compound of Example 54A, 1 ml of water and 1 ml of methanol, and the mixture was stirred at 40° C. for 1.5 h. An additional 6 mg (75 μmol) of potassium cyanate were added, and stirring of the reaction mixture was continued at RT overnight. A few ml of DMSO were added, and the entire solution was separated by preparative HPLC [Method 8]. The product fraction was freed from the solvent on a rotary evaporator and the residue was dried under high vacuum. This gave 17 mg (56% of theory) of the title compound.

Workup

  1. stirringstirring of the reaction mixture
  2. waitwas continued at RT overnight
  3. customthe entire solution was separated by preparative HPLC [Method 8]
  4. customThe product fraction was freed from the solvent on a rotary evaporator
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-602ca95d42334bfcb795f054f972759a
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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