2-bromo-N-isopropyl-N-phenyl-acetamide → 2-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide

HRID 900133Notes

Reaction equation

HRID 900133 reaction equation
[CH:1]1([C:7]2[N:16]3[C:10]([CH2:11][C:12](=[O:36])[N:13]([CH2:21][C:22]([N:24]([CH:33]([CH3:35])[CH3:34])[C:25]4[CH:26]=N[C:28](OC)=[CH:29][CH:30]=4)=[O:23])[C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:37]1(C2N3C(CC(=O)NC4C=CC=CC=43)=NN=2)CCCCC1.BrCC(N(C(C)C)C1C=CC=CC=1)=O>>[CH:1]1([C:7]2[N:16]3[C:10]([CH2:11][C:12](=[O:36])[N:13]([CH2:21][C:22]([N:24]([CH:33]([CH3:34])[CH3:35])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:37][CH:26]=4)=[O:23])[C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 152160012-bromo-N-isopropyl-N-phenyl-acetamideHCID 589579321-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-oneHCID 589579462-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide

Product 1

HCID 693139642-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide

Procedure

Following the procedure described for Preparation 8(A), 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one (Preparation 4(B) (640 mg, 0.226 mmol) was alkylated with 2-bromo-N-isopropyl-N-phenyl-acetamide (Preparation 1(A)) (580 mg, 0.226 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (CH2Cl2 to 4% MeOH in CH2Cl2) provided 668 mg of 2-(1-cyclohexyl-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide. 1H NMR (CDCl3) δ 7.62-7.31 (m, 9), 4.93 (m, 1), 4.10 (d, 1), 3.91 (d, 1), 3.76 (d, 1), 3.45 (d, 1), 2.85 (m, 1), 2.19 (br. d., 1), 1.91 (m, 2), 1.69-1.11 (m, 7), 1.06 (m, 6): MS 458.4 (M+1).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (CH2Cl2 to 4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-984d1a65a2be415ba0c44583936a5fca
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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