Hydrochloric Acid → HCID 178457046, compound

HRID 900107Notes

Reaction equation

HRID 900107 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]=[CH:35][CH:36]=[CH:37][C:21]=3[N:20]([CH2:38][C:39](=[O:51])[N:40]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:41]([CH3:43])[CH3:42])[C:19]2=[O:52])=[N:9]1)=O)(C)(C)C.Cl>CCOC(C)=O>[CH2:44]([N:40]([CH:41]([CH3:43])[CH3:42])[C:39](=[O:51])[CH2:38][N:20]1[C:19](=[O:52])[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]=[CH:35][CH:36]=[CH:37][C:21]1=2)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 693126163-(6-[(benzyl-isopropyl-carbamoyl)-methyl]-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 178457046HCID 178457046, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in Example 3(B), Step B, 3-{6-[(benzyl-isopropyl-carbamoyl)-methyl]-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl}-indazole-1-carboxylic acid tertbutyl ester (19.1 mg, 0.274 mmol) was deprotected with HCl (4.0M in dioxane, 0.8 mL) over 24 hours. The reaction was diluted with EtOAc, and the organic solution was washed with aqueous NaHCO3 (1×), dried (Na2SO4), filtered and concentrated. Purification by preparative chromatography eluting with 5% MeOH in CH2Cl2 provided 8.5 mg of N-benzyl-2-[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 as a racemic mixture. 1H NMR (CD2Cl2) δ 7.97 (t, 1H), 7.12-7.64 (m, 15H), 7.05 (m, 1H), 6.92 (m, 1H), 5.08 (d) and 4.81 (d, total 1H), 4.60-4.74 (m, 2H), 4.49 (s, 1H), 4.45 (t, 1H), 4.29-4.39 (m, 1H), 3.96-4.13 (m, 2H), 1.16 (dd, 3H), 1.05 (dd, 3H); MS 596.2 (M+1), 594.2 (M−1).

Workup

  1. washthe organic solution was washed with aqueous NaHCO3 (1×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative chromatography
  6. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-60c3295dbfdf4302af3306a405b0a8e7
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

Loading…