Hydrochloric Acid → HCID 58957912, compound

HRID 900109Notes

Reaction equation

HRID 900109 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2([CH3:52])[C:27]3[N:23]([C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:25][N:26]=3)[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[N:20]([CH2:38][C:39](=[O:50])[N:40]([CH:47]([CH3:49])[CH3:48])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:19]2=[O:51])=[CH:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2([CH3:52])[C:27]3[N:23]([C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:25][N:26]=3)[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[N:20]([CH2:38][C:39]([N:40]([CH:47]([CH3:48])[CH3:49])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:50])[C:19]2=[O:51])=[CH:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69311148HCID 69311148, compound

Product 1

HCID 58957912HCID 58957912, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-{6-[(isopropyl-phenyl-carbamoyl)-methyl]-4-methyl-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl}-indole-1-carboxylic acid tert-butyl ester in dioxane (1 mL) was added HCl (4.0M in dioxane, 550 μL) and the reaction was stirred at room temperature for 50 hours. The volatiles were concentrated in vacuo and the residue was dissolved in CH2Cl2. The organic solution was washed with aqueous NaHCO3 (1×), dried (Na2SO4), filtered and concentrated. Purification by preparative chromatography eluting with 40% acetone in CH2Cl2 provided 17 mg of 2-[4-(1H-indol-3-ylmethyl)-4-methyl-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD2Cl2) δ 8.37 (s, 1H), 7.78 (m, 1H), 7.53-7.23 (m, 13H), 7.11 (m, 2H), 7.02 (t, 1H), 6.90 (d, 1H), 5.03 (m, 1H), 4.33 (d, 1H), 3.76-3.58 (m, 1H), 2.83 (m, 2H), 1.75 (s, 3H), 1.11 (m, 6H); MS 595.2 (M+1).

Workup

  1. concentrationThe volatiles were concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organic solution was washed with aqueous NaHCO3 (1×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative chromatography
  8. washeluting with 40% acetone in CH2Cl2

Sources & evidence

ORD record
ord-30e9ed24cdbc421aaef2d59a6e2668cc
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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