N-Butyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide monosulphate salt → N-Butyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

HRID 1255336Notes

Reaction equation

HRID 1255336 reaction equation
S(O)(O)(=O)=O.[CH2:6]([N:10]([CH2:47][CH2:48][NH:49][CH2:50][CH2:51][C:52]1[C:57]2[O:58][CH2:59][C:60](=[O:62])[NH:61][C:56]=2[C:55]([OH:63])=[CH:54][CH:53]=1)[C:11](=[O:46])[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][N:25]2[CH2:45][CH2:44][C:28]3([O:33][CH2:32][CH2:31][N:30]([C:34]([C:36]4[N:37]=[C:38]([CH:41]([CH3:43])[CH3:42])[S:39][CH:40]=4)=[O:35])[CH2:29]3)[CH2:27][CH2:26]2)[CH:18]=1)[CH2:7][CH2:8][CH3:9]>C(Cl)Cl.CO>[CH2:6]([N:10]([CH2:47][CH2:48][NH:49][CH2:50][CH2:51][C:52]1[C:57]2[O:58][CH2:59][C:60](=[O:62])[NH:61][C:56]=2[C:55]([OH:63])=[CH:54][CH:53]=1)[C:11](=[O:46])[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][N:25]2[CH2:45][CH2:44][C:28]3([O:33][CH2:32][CH2:31][N:30]([C:34]([C:36]4[N:37]=[C:38]([CH:41]([CH3:42])[CH3:43])[S:39][CH:40]=4)=[O:35])[CH2:29]3)[CH2:27][CH2:26]2)[CH:18]=1)[CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 1

HCID 86651693N-Butyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide monosulphate salt

Product 1

HCID 51036603N-Butyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

N-Butyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide Sulphate salt Modification A (Example 34a) (1.73 g) was dissolved in DCM/methanol, filtered and evaporated to dryness. The resultant gum was partitioned between sat aq bicarb (100 mL) and freshly distilled MeTHF (150 mL) and the mixture stirred vigorously for 10 mins. The organic layer was separated, washed with fresh sodium bicarbonate (×2), dried over sodium sulphate, filtered and evaporated under reduced pressure to give the title compound as a foam. Yield 1.2 g.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe resultant gum was partitioned
  4. customThe organic layer was separated
  5. washwashed with fresh sodium bicarbonate (×2)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9ed9b2720d69428785a33edb6e6f90a0
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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