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

HRID 900131

Reaction equation

HRID 900131 reaction equation
[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[CH2:15][C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2].C(OC1CC(=O)N(CC(N(C(C)C)C2C=CC=CC=2)=O)C2C=CC=CC=2N=1)C.[F:63]C1C=CC=CC=1C(NN)=O>>[F:63][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:11]1[N:10]2[C:14]([CH2:15][C:16](=[O:17])[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:28])[C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=32)=[N:13][N:12]=1

Participants

4

Reactant 3

HCID 1362882-FluorobenzhydrazideHCID 589579362-(4-ethoxy-2-oxo-2,3-dihydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide2×HCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

Product 1

HCID 693140432-(1-(2-fluorophenyl)-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 7(A), 2-(4-ethoxy-2-oxo-2,3-dihydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (Preparation 5(B) (200 mg, 0.527 mmol) is reacted with 2-fluorobenzhydrazide (81 mg, 0.527 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (CH2Cl2 to 3% MeOH in CH2Cl2) provided 180.2 mg of 2-(1-(2-fluorophenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD2Cl2) δ 7.73 (m, 1), 7.64 (d, 1), 7.91-7.18 (m, 8), 7.12-7.00 (m, 2), 6.83 (d, 1), 4.96 (m, 1), 4.23 (d, 1), 4.06 (d, 1), 3.80 (d, 1), 3.58 (d, 1), 1.09 (d, 6); MS 470.3 (M+1)

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (CH2Cl2 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0e841fd731e54d14b0b1b6c13ba2ae22
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Linked notes

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