Dimethylformamide → 4-[4-(3-Indolyl)piperidinomethyl]-2-cyclopropylcarbonylaminothiazole

HRID 1252074Notes

Reaction equation

HRID 1252074 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.C(N(CC)CC)C.CN(C)C=O.[CH:35]1([C:38](Cl)=[O:39])[CH2:37][CH2:36]1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:38]([CH:35]4[CH2:37][CH2:36]4)=[O:39])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 141297964-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-amine

Product 1

HCID 103397554-[4-(3-Indolyl)piperidinomethyl]-2-cyclopropylcarbonylaminothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[4-(3-indolyl)piperidinomethyl]-2-aminothiazole (3.0 g), triethylamine (5.4 ml) and N,N-dimethylformamide (30 ml) was added dropwise a solution of cyclopropylcarbonyl chloride (2.18 ml) in methylene chloride (2.5 ml) over a period of 30 minutes at 0° C. in a stream of nitrogen gas with stirring. After the reaction was finished, the reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V) to give 4-[4-(3-indolyl)piperidinomethyl]-2-cyclopropylcarbonylaminothiazole (2.9 g).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V)

Sources & evidence

ORD record
ord-afe5bb6c294648b39b3fba9f07d2f8fb
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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