1-Aminohomopiperidine → 5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)-n-(hexahydro(1 h)azepin-1-yl)thiazole-2-carboxamide

HRID 1392370Notes

Reaction equation

HRID 1392370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](O)=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.[NH2:24][N:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C1C=NC2N(O)N=NC=2C=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([NH:24][N:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 221981-AminohomopiperidineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10045599HCID 10045599, compoundHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphate

Product 1

HCID 101280125-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)-n-(hexahydro(1 h)azepin-1-yl)thiazole-2-carboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: To a solution of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid (0.50 gram, 1.30 mmol) in dichloromethane (10 mL) is successively added 1-aminohexahydro(1H)azepine (0.15 gram, 1.30 mmol), 7-aza-1-hydroxybenzotriazole (0.18 gram, 1.30 mmol), 7-azabenzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyAOP) (0.68 gram, 1.30 mmol) and diisopropylethylamine (0.34 mL, 1.95 mmol) and the resulting solution is stirred for 1 hour at room temperature. Concentration In vacuo gives a crude oil (2.01 gram) which is purified by flash chromatography (ethyl acetate/petroleum ether=1/3 (v/v)) to give 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(hexahydro(1 H)azepin-1-yl)thiazole-2-carboxamide (0.350 gram, 56% yield). Melting point: 185-186° C. (after recrystallisation from diisopropyl ether).

Workup

  1. concentrationConcentration In vacuo
  2. customgives a crude oil (2.01 gram) which
  3. customis purified by flash chromatography (ethyl acetate/petroleum ether=1/3 (v/v))

Sources & evidence

ORD record
ord-3e182a822c1548e18073debe78a55a87
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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