Methyl 2-(4-aminopiperidin-1-yl)-1,3-thiazole-5-carboxylate → Methyl 2-(4-{[(3,4-dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 2234029Notes

Reaction equation

HRID 2234029 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=2)[CH2:4][CH2:3]1.[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([C:24]#[N:25])[NH:20][C:19]=1[C:26](Cl)=[O:27]>C1COCC1>[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([C:24]#[N:25])[NH:20][C:19]=1[C:26]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=2)[CH2:4][CH2:3]1)=[O:27]

Participants

4

Reactant 2

HCID 68579838Methyl 2-(4-aminopiperidin-1-yl)-1,3-thiazole-5-carboxylate2×HCID 860383333,4-Dichloro-5-cyano-1H-pyrrole-2-carbonyl chloride2×

Product 1

HCID 68580069Methyl 2-(4-{[(3,4-dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

TEA (0.06 ml, 0.5 mmol) was added to a solution of methyl 2-(4-aminopiperidin-1-yl)-1,3-thiazole-5-carboxylate (Intermediate 134, 0.1 g, 0.5 mmol)) in anhydrous THF. To this was added 3,4-dichloro-5-cyano-1H-pyrrole-2-carbonyl chloride (Intermediate 132, 0.1 g, 0.5 mmol) as a solution in anhydrous THF. After stirring 15 minutes, THF was removed. The product was partitioned with EtOAc and water. The organic portion was dried with MgSO4 and concentrated to a yellow oil. Trituration with ether followed by filtration yielded a tan solid.

Workup

  1. customTHF was removed
  2. customThe product was partitioned with EtOAc and water
  3. dry with materialThe organic portion was dried with MgSO4
  4. concentrationconcentrated to a yellow oil
  5. filtrationTrituration with ether followed by filtration
  6. customyielded a tan solid

Sources & evidence

ORD record
ord-cb69b010b6ec4119801c6729afda27e5
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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