Ammonia → HCID 12109358, compound

HRID 2116542Notes

Reaction equation

HRID 2116542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][C:22]3[CH:23]=[C:24]([Cl:28])[CH:25]=[N:26][CH:27]=3)=[C:16]([CH:20]=2)[C:17](O)=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH3:33]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][C:22]3[CH:23]=[C:24]([Cl:28])[CH:25]=[N:26][CH:27]=3)=[C:16]([CH:20]=2)[C:17]([NH2:33])=[O:18])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 12109357HCID 12109357, compound

Product 1

HCID 12109358HCID 12109358, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of the acid from Example 10 (20 mg, 0.046 mmol) in CH2Cl2 (0.5 mL) and pyridine (0.5 mL) was added thionyl chloride (17 mL, 0.228 mmol). After one hour, the solution was evaporated and placed under vacuum overnight. The residue was then dissolved in MeOH (1 mL) and CH2Cl2 (1 mL) and NH3 (0.12 mL, 0.227 mmol, 0.757 M solution in ethanol) was added dropwise. The mixture was stirred for 8 hours and the solvent was evaporated. The residue was purified by chromatography (1:1 hexane/diethyl ether) to yield 7.3 mg of the title compound (37%).

Workup

  1. customthe solution was evaporated
  2. customplaced under vacuum overnight
  3. dissolutionThe residue was then dissolved in MeOH (1 mL)
  4. customthe solvent was evaporated
  5. customThe residue was purified by chromatography (1:1 hexane/diethyl ether)

Sources & evidence

ORD record
ord-9b0053abbacb412280a16b916e639bc8
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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