Triethylamine → N-[1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-N-cyclopropyl-4-oxazol-5-yl-benzamide

HRID 68835Notes

Reaction equation

HRID 68835 reaction equation
Cl.[CH:2]1([N:5]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:6](=[O:18])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][CH:16]=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:4][CH2:3]1.[Cl:25][C:26]1[N:30]=[C:29](Cl)[S:28][N:27]=1.C(N(CC)CC)C>ClCCl>[Cl:25][C:26]1[N:30]=[C:29]([N:22]2[CH2:23][CH2:24][CH:19]([N:5]([CH:2]3[CH2:4][CH2:3]3)[C:6](=[O:18])[C:7]3[CH:8]=[CH:9][C:10]([C:13]4[O:17][CH:16]=[N:15][CH:14]=4)=[CH:11][CH:12]=3)[CH2:20][CH2:21]2)[S:28][N:27]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2725055Dichloro-1,2,4-thiadiazoleHCID 68289930N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide hydrochloride

Product 1

HCID 68290214N-[1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-N-cyclopropyl-4-oxazol-5-yl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide hydrogen chloride salt (696 mg), 3,5-dichloro-1,2,4-thiadiazole (372 mg), and triethylamine (0.42 mL) in dichloromethane (30 mL) is stirred overnight at room temperature. More triethylamine (0.40 mL) is added and the mixture is stirred until the conversion is complete (1 h). The solvent is partly evaporated and the residue is triturated with water. The precipitate is filtered off, washed with dichloromethane and dried to yield the title compound. LC (method 5): tR=2.08 min; Mass spectrum (ESI+): m/z=430/432 (Cl) [m+H]+.

Workup

  1. stirringthe mixture is stirred until the conversion
  2. custom(1 h)
  3. customThe solvent is partly evaporated
  4. customthe residue is triturated with water
  5. filtrationThe precipitate is filtered off
  6. washwashed with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-167d80cfc81f48c79b865e35021a37d7
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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