Aniline → HCID 57541255, compound

HRID 421737Notes

Reaction equation

HRID 421737 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8](C)[S:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:32]=[CH:31][C:20]3=[N:21][CH:22]=[C:23]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)[CH:24]=[C:19]3[C:18](=[O:33])[C:17]=2[CH:34]=1)(=[O:11])=[O:10].N[C:37]1[CH:42]=[CH:41]C=[CH:39][CH:38]=1>O1CCOCC1.O>[CH3:30][N:28]1[CH:29]=[C:25]([C:23]2[CH:24]=[C:19]3[C:18](=[O:33])[C:17]4[CH:34]=[C:13]([CH2:12][S:9]([NH:8][C:7]5[CH:41]=[CH:42][CH:37]=[CH:38][CH:39]=5)(=[O:10])=[O:11])[CH:14]=[CH:15][C:16]=4[CH:32]=[CH:31][C:20]3=[N:21][CH:22]=2)[CH:26]=[N:27]1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 23653618HCID 23653618, compound

Product 1

HCID 57541255HCID 57541255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

Cesium carbonate (80 mg, 0.245 mmol) was added to a solution of N,N-dimethyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]methanesulfonamide (50 mg, 0.122 mmol) and aniline (559 μL, 6.12 mmol) in dioxane (1113 μl) and water (111 μl) in a 0.5 ml to 2 ml microwave vial. The vial was then sealed and the mixture was heated to 180° C. for 3 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.1% TFA, to afford the title compound as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 9.84 (br s, 1H); 9.22 (d, 1H); 8.51 (d, 1H); 8.48 (s, 1H); 8.15 (s, 1H); 8.04 (d, 1H); 7.76 (d, 1H); 7.63 (dd, 1H); 7.38 (d, 1H); 7.32 (d, 1H); 7.27 (m, 2H); 7.16 (dd, 2H); 7.00 (m, 1H); 4.68 (s, 2H); 3.89 (s, 3H). LRMS (APCI) calculated for C25H21N4O3S [M+H]+, 457.1; found 457.1.

Workup

  1. customThe vial was then sealed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  5. washeluting with Acetonitrile/Water+0.1% TFA

Sources & evidence

ORD record
ord-28296955828d4013b6a7653d8627b700
Source dataset
uspto-grants-2012_01
Patent number
US08101603B2

Reaction notes

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