Sodium Bicarbonate → HCID 14129814, compound

HRID 1252069Notes

Reaction equation

HRID 1252069 reaction equation
[CH3:1][NH:2][C:3](=[O:12])[NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]Cl)[N:9]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([CH2:10][C:8]3[N:9]=[C:5]([NH:4][C:3]([NH:2][CH3:1])=[O:12])[S:6][CH:7]=3)[CH2:14][CH2:15]2)=[CH:20]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 20140943HCID 20140943, compound

Product 1

HCID 14129814HCID 14129814, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a stream of nitrogen gas, a mixture of 2-(3-methylureido)-4-chloromethylthiazole (1.0 g), 3-(4-piperidyl)indole (0.98 g), sodium hydrogen carbonate (0.45 g) and N,N-dimethylformamide (5 ml) was heated at 80° to 90° C. The reaction mixture was then concentrated and the residue was subjected to column chromatography on silica gel. Elution was carried out with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the desired compound were collected and concentrated under reduced pressure. The residue was precipitated with n-hexane to give 4-[4-(3-indolyl)piperidinomethyl]-2-(3-methylureido)thiazole (540 mg).

Workup

  1. temperaturewas heated at 80° to 90° C
  2. concentrationThe reaction mixture was then concentrated
  3. washElution
  4. additionwas carried out with a mixture of chloroform and methanol (10:1 V/V)
  5. additionThe fractions containing the desired compound
  6. customwere collected
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was precipitated with n-hexane

Sources & evidence

ORD record
ord-fa88eb491c334c85ac1a45eaae895265
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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