Hydrochloric Acid → HCID 178480061, compound

HRID 68449Notes

Reaction equation

HRID 68449 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:12])(=[O:11])[N:9]([C:13]3[C:14]([C:41]([CH3:49])([CH3:48])[O:42][SiH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[C:15]([C:19]4[CH:20]=[C:21]([NH:26][C:27]5[CH:32]=[CH:31][C:30]([C:33]([N:35]6[CH2:40][CH2:39][O:38][CH2:37][CH2:36]6)=[O:34])=[CH:29][N:28]=5)[C:22](=[O:25])[NH:23][CH:24]=4)[CH:16]=[CH:17][CH:18]=3)[CH2:8][CH2:7][C:6]=2[CH:50]=1.Cl.[C:52]([O-])([O-])=O.[Na+].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:11])(=[O:12])[N:9]([C:13]3[C:14]([C:41]([CH3:49])([CH3:48])[O:42][SiH2:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[C:15]([C:19]4[CH:20]=[C:21]([NH:26][C:27]5[CH:32]=[CH:31][C:30]([C:33]([N:35]6[CH2:36][CH2:37][O:38][CH2:39][CH2:40]6)=[O:34])=[CH:29][N:28]=5)[C:22](=[O:25])[N:23]([CH3:52])[CH:24]=4)[CH:16]=[CH:17][CH:18]=3)[CH2:8][CH2:7][C:6]=2[CH:50]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 178455419HCID 178455419, compound

Product 1

HCID 178480061HCID 178480061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 5-[3-(6-Bromo-1,1-dioxo-3,4-dihydro-1H-1lambda*6*-benzo[e][1,2]thiazin-2-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one (0.05 g, 0.06 mmol), conc. HCl (1 mL) in methanol (10 mL) was stirred rt for 30 min. The mixture was neutralized with solid Na2CO3 and concentrated to afford a dark residue. Purification by silica gel chromatography (methylene chloride/acetone) afforded 0.01 g of 5-[3-(6-bromo-1,1-dioxo-3,4-dihydro-1H-1lambda*6*-benzo[e][1,2]thiazin-2-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-1-methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one as a pale solid MS (ESI) 682.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customto afford a dark residue
  3. customPurification by silica gel chromatography (methylene chloride/acetone)

Sources & evidence

ORD record
ord-97c0ff046066455baf35cb686b81a945
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Reaction notes

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