Water → HCID 57950351, compound

HRID 1020675Notes

Reaction equation

HRID 1020675 reaction equation
[C:1](Cl)([CH3:3])=[O:2].[CH3:5][N:6]1[C:14]2[CH:13]=[C:12]([N:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=4)=[CH:17][C:16]3=[O:31])[CH:11]=[CH:10][C:9]=2[C:8]2[CH2:32][NH:33][CH2:34][CH2:35][C:7]1=2.CCN(CC)CC.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([N:33]1[CH2:34][CH2:35][C:7]2[N:6]([CH3:5])[C:14]3[CH:13]=[C:12]([N:15]4[CH:20]=[CH:19][C:18]([C:21]5[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][N:22]=5)=[CH:17][C:16]4=[O:31])[CH:11]=[CH:10][C:9]=3[C:8]=2[CH2:32]1)(=[O:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 44193994HCID 44193994, compound

Product 1

HCID 57950351HCID 57950351, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

AcCl (0.03 mL, 0.4 mmol) was added to a solution of 1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one (125 mg, 0.294 mmol), DMAP (7 mg, 0.06 mmol) and Et3N (0.08 mL, 0.6 mmol) in CH2Cl2 (10 mL) under N2, and the resulting solution was stirred at 25° C. for 17 h. H2O was added to the solution, and the phases were separated. The organic phase was washed with saturated NH4Cl solution, dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded the title compound (116 mg, 84%) as a mixture of rotomers as a white powder: mp 232-236° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.15 (s, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.35 (d, J=8.3 Hz, 1H), 7.84 (d, J=7.5 Hz, 1H), 7.59-7.54 (m, 2H), 7.28 (d, J=1.5 Hz, 1H), 7.08-7.03 (m, 2H), 4.70 (s, 0.8H), 4.68 (s, 1.2H), 3.88 (t, J=5.5 Hz, 0.8H), 3.83 (t, J=5.5 Hz, 1.2H), 3.67 (s, 3H), 2.97-2.91 (m, 1.2H), 2.86-2.81 (m, 0.8H), 2.15 (s, 1.8H), 2.13 (s, 1.2H); ESI MS m/z 467 [M+H]+.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with saturated NH4Cl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96abedb18018472d8423d08095183288
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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