Indole-3-Carboxaldehyde → HCID 131726820, compound

HRID 900090Notes

Reaction equation

HRID 900090 reaction equation
C(OC1C=C(C2N3C(CC(=O)N([CH2:29][C:30]([N:32]([CH:41]([CH3:43])[CH3:42])[C:33]4[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[O:31])C4C=CC=CC=43)=NN=2)C=CC=1)C1C=CC=CC=1.N1C2C(=CC=CC=2)C(C=O)=C1>>[CH:41]([N:32]([C:33]1[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1)[C:30](=[O:31])[CH3:29])([CH3:42])[CH3:43]

Participants

3

Reactant 2

HCID 10256Indole-3-CarboxaldehydeHCID 58957948HCID 58957948, compound

Product 1

HCID 131726820HCID 131726820, compound

Procedure

Following the procedure described for Example 1(A), Step A, 2-[1-(3-benzyloxy-phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide (Preparation 6) (129 mg, 0.219 mmol) was condensed with 1H-indole-3-carbaldehyde (70 mg, 0.48 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc) yielded 60 mg of 2-[1-(3-benzyloxy-phenyl)-4-1H-indol-3-ylmethylene)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. 1H NMR (CD3OD) δ 8.13 (m, 1H), 7.64 (m, 2H), 7.23-7.48 (m, 3H), 7.13 (m, 3H), 6.93 (m, 2H), 4.94 (m, 2H), 4.85 (m, 1H), 4.63 (m, 1H), 4.20-4.40 (m, 1H), 3.96 (m, 1H), 3.85 (d, 1H), 0.90-1.05 (m, 6H); MS 716.5 (M+1), 714.6 (M−1)

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-bae08b47e203432a94a3f84571521c48
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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