Thiourea → HCID 44137768, compound

HRID 2363707Notes

Reaction equation

HRID 2363707 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[N:13]=2)[CH:10]=1)=O.[NH2:23][C:24]([NH2:26])=[S:25]>CO>[NH2:26][C:24]1[S:25][CH:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]3[N:9]([CH:11]=[C:12]([C:14]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:15])[N:13]=3)[CH:10]=2)[N:23]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 44136066HCID 44136066, compound

Product 1

HCID 44137768HCID 44137768, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 60 mg of crude 6-(2-bromoacetyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in 10 mL of methanol are added 14 mg of thiourea. The reaction mixture is heated for 45 minutes at reflux and then concentrated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, eluting with a mixture of dichloromethane and methanol (gradient of from 100/0 to 90/10). The fractions containing the expected product are combined and evaporated to dryness under reduced pressure to give 20 mg of 6-(2-aminothiazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe reaction mixture is heated for 45 minutes
  2. temperatureat reflux
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue is chromatographed on a silica cartridge
  5. washeluting with a mixture of dichloromethane and methanol (gradient of from 100/0 to 90/10)
  6. additionThe fractions containing the expected product
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d6c4caf7df704c5fb907fa0fe635becd
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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