Hydrochloric Acid → HCID 178457047, compound

HRID 900105Notes

Reaction equation

HRID 900105 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][CH:18]2[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]=[C:35]([F:39])[C:36]([F:38])=[CH:37][C:21]=3[N:20]([CH2:40][C:41](=[O:53])[N:42]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:43]([CH3:45])[CH3:44])[C:19]2=[O:54])=[N:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:46]([N:42]([CH:43]([CH3:45])[CH3:44])[C:41](=[O:53])[CH2:40][N:20]1[C:19](=[O:54])[CH:18]([CH2:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][N:9]=2)[C:27]2[N:23]([C:24]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:25][N:26]=2)[C:22]2[CH:34]=[C:35]([F:39])[C:36]([F:38])=[CH:37][C:21]1=2)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 693127063-{6-[(benzyl-isopropyl-carbamoyl)-methyl]-8,9-difluoro-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl}-indazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 178457047HCID 178457047, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-{6-[(benzyl-isopropyl-carbamoyl)-methyl]-8,9-difluoro-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl}-indazole-1-carboxylic acid tert-butyl ester (100 mg, 0.137 mmol) in dioxane (1 mL) was added HCl (4.0M in dioxane, 2 mL). The reaction was stirred at room temperature for 24 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 in vacuo. Purification by preparative chromatography eluting with 5% MeOH in CH2Cl2 provided 45 mg of N-benzyl-2-[8,9-difluoro-4-(1H-indazol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-acetamide. 1H NMR (CD2Cl2) δ 7.92 (m, 1H), 7.04-7.66 (m, 14H), 6.67 (s, 1H), 4.22-4.96 (m, 6H), 3.91-4.13 (m, 2H), 1.01-1.22 (m, 6H); MS 632.3 (M+1), 630.2 (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 in vacuo
  7. customPurification by preparative chromatography
  8. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-c4eb4b9aa9144924a57fe1e7b42165b2
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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