Triethylamine → HCID 67270810, compound

HRID 1696544Notes

Reaction equation

HRID 1696544 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N:24]4[C:28](C(O)=O)=[CH:27][C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])=[N:25]4)[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:38]([CH2:41]C)CC.[Cl:43][C:44]1[C:50]([Cl:51])=[CH:49][CH:48]=[CH:47][C:45]=1[NH2:46].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:59])=CC=1>C1(C)C=CC=CC=1>[C:32]([C:26]1[CH:27]=[C:28]([NH:38][C:41]([NH:46][C:45]2[CH:47]=[CH:48][CH:49]=[C:50]([Cl:51])[C:44]=2[Cl:43])=[O:59])[N:24]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:23]=[CH:22]3)[N:25]=1)([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118442,3-DichloroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 67271320HCID 67271320, compound

Product 1

HCID 67270810HCID 67270810, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(2-(4-(t-butoxycarbonyl)piperazin-1-yl)quinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylic acid (0.1 g, 0.21 mmol) in toluene (2 mL) was added Et3N (0.032 mL, 0.23 mmol) and 2,3-dichloroaniline (84 mg, 0.52 mmol). The reaction mixture was stirred at RT and DPPA (63 mg, 0.23 mmol) was added. The reaction mixture was heated at 100° C. for 2 h, cooled, quenched with H2O, and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried (Na2SO4), concentrated and purified by column chromatography to yield t-butyl 4-(6-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)quinolin-2-yl)piperazine-1-carboxylate (0.11 g, 83% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.26 (s, 1H), 8.77 (s, 1H), 8.17 (d, J=9.6 Hz, 1H), 8.07 (dd, J=3.2, and 6.8 Hz, 1H), 7.87 (d, J=2.0 Hz, 1H), 7.68 (m, 2H), 7.31 (m, 3H), 6.42 (s, 1H), 3.74 (m, 4H), 3.47 (m, 4H), 1.44 (s, 9H), 1.30 (s, 9H); LC-MS (EI) m/z: 638.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated at 100° C. for 2 h
  2. temperaturecooled
  3. customquenched with H2O
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-ee921de948b742e3bae351cc8973b8ad
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…