Dimethylamine → HCID 50994357, compound

HRID 1784852Notes

Reaction equation

HRID 1784852 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:19].[CH:30]([N:33]([CH:36](C)C)[CH2:34]C)(C)C.CNC>C(Cl)Cl.C1COCC1.N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:34](=[O:19])[N:33]([CH3:36])[CH3:30])[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 50994432(3-Amino-5-bromo-phenyl)-pyridin-3-yl-methanone

Product 1

HCID 50994357HCID 50994357, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 0.2 g (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 5 mL of methylene chloride was added 0.16 g of 4-nitrophenyl chloroformate (0.79 mmol) and 0.12 mL of pyridine. An additional 10 mL of methylene chloride was added, and the reaction was stirred for 3 hours at room temperature at which time 0.15 mL (0.866 mmol) diisopropylethyl amine and 0.873 mL (1.75 mmol) 2 N dimethylamine in THF were added. The reaction was stirred at ambient temperature overnight, then transferred to a separatory funnel. The methylene chloride phase was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated. The crude product was chromatographed to give 3-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-1,1-dimethyl-urea. This material was converted to 3-[3-(1H-Indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-1,1-dimethyl-urea as described for Example 75. 1H NMR (400 MHz, CD3OD) δ 8.97 (s, 1H), 8.75 (d, J=3.7 Hz, 1H), 8.25 (td, J=7.9, 1.9 Hz, 1H), 8.09 (t, J=1.9 Hz, 1H), 7.84 (t, J=1.9 Hz, 1H), 7.73 (t, J=1.6 Hz, 1H), 7.58 (dd, J=7.8, 4.9 Hz, 1H), 7.39 (td, J=8.0, 1.0 Hz, 1H), 7.28 (d, J=3.1 Hz, 1H), 7.17 (t, J=7.6 Hz, 1H), 7.12 (dd, J=7.3, 1.1 Hz, 1H), 6.67 (dd, J=3.1, 1.0 Hz, 1H), 3.02 (s, 6H).

Workup

  1. additionwere added
  2. customtransferred to a separatory funnel
  3. washThe methylene chloride phase was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-1895ad04c203471ca6ad0e5b449f9b51
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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