Potassium Carbonate → 1-Benzyl-6-({3-[4-(1,3-thiazol-2-ylcarbonyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 1911133Notes

Reaction equation

HRID 1911133 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:17][N:16]([C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[NH:26][CH2:25][CH2:24][CH2:23]4)=[O:19])[CH2:15]2)[CH2:10][CH2:9]1)=[O:7].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:18]([N:26]1[C:27]2[C:22](=[CH:21][C:20]([C:18]([N:16]3[CH2:17][CH:14]([N:11]4[CH2:12][CH2:13][N:8]([C:6]([C:2]5[S:1][CH:5]=[CH:4][N:3]=5)=[O:7])[CH2:9][CH2:10]4)[CH2:15]3)=[O:19])=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH2:25]1)[C:20]1[CH:21]=[CH:22][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 498009896-(3-[4-(1,3-Thiazol-2-ylcarbonyl)piperazin-1-yl]-azetidin-1-yl)carbonyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 596258021-Benzyl-6-({3-[4-(1,3-thiazol-2-ylcarbonyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinolineYield 764.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 357 (30 mg, 0.0073 mmol) in CH3CN (1 mL) was added compound 18a (0.01 mL, 0.0088 mmol), followed by the addition of K2CO3 (20 mg, 0.015 mmol). The reaction mixture was stirred at room temperature for 18 h. The resultant mixture was partitioned between CH2Cl2 and H2O. The organic solution was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 1% MeOH/EtOAc+0.5% Et3N) gave compound 370 (14 mg). 1H NMR (400 MHz, CDCl3): δ 7.88 (d, J=3.3 Hz, 1H), 7.54 (d, J=3.0 Hz, 1H), 7.38 (d, J=2.0 Hz, 1H), 7.30-7.36 (m, 2H), 7.19-7.30 (m, 4H), 6.44 (d, J=8.6 Hz, 1H), 4.54 (s, 2H), 3.97-4.52 (m, 6H), 3.77-3.96 (m, 2H), 3.40-3.47 (m, 2H), 3.15-3.24 (m, 1H), 2.83 (t, J=6.2 Hz, 2H), 2.38-2.59 (m, 4H), 1.98-2.05 (m, 2H); LC/MS m/z (M+H+) 502.2.

Workup

  1. customThe resultant mixture was partitioned between CH2Cl2 and H2O
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by flash column chromatography (silica gel, 1% MeOH/EtOAc+0.5% Et3N)

Sources & evidence

ORD record
ord-cd120bdb76ec4ae6a6b7620814235b49
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

Loading…