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Triethylamine → HCID 178490722, compound

HRID 641275
Notes
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Reaction equation

HRID 641275 reaction equation
[ClH:1].[NH2:2][OH:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([S:31]([C:34]4[CH:39]=[C:38](Cl)[CH:37]=[CH:36][C:35]=4[O:41][CH3:42])(=[O:33])=[O:32])[C:26]=3[CH:43]=2)=[O:21])=[CH:15][CH:14]=1)#[N:12]>CS(C)=O.O>[OH:3][NH:2][C:11]([C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([S:31]([C:34]4[CH:39]=[C:38]([Cl:1])[CH:37]=[CH:36][C:35]=4[O:41][CH3:42])(=[O:32])=[O:33])[C:26]=3[CH:43]=2)=[O:21])=[CH:17][CH:18]=1)=[NH:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 667886204-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide

Product 1

HCID 178490722HCID 178490722, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Procedure

A solution of hydroxylamine hydrochloride (90 mg, 1.3 mmol) in dimethyl sulfoxide (1.25 mL) was treated with triethylamine (131 mg, 0.18 mL, 1.3 mmol) and stirred at room temperature for 5 min. The solids were filtered off, and 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide (125 mg, 0.26 mmol) was added. The mixture was stirred at 75° C. for 1.5 hours. After cooling back to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was extracted three times with 0.5N HCl. The combined acidic aqueous layer was then rebasified with 1N NaOH and extracted three times with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and evaporated. 4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide was obtained as a white solid, 97 mg (73%), MS (ISP): m/e=517.0 (M+H+.).

Workup

  1. filtrationThe solids were filtered off
  2. stirringThe mixture was stirred at 75° C. for 1.5 hours
  3. temperatureAfter cooling back to room temperature
  4. extractionextracted with ethyl acetate
  5. extractionThe organic phase was extracted three times with 0.5N HCl
  6. extractionextracted three times with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-d33176ccaa714c3a9febb1bdb607c2c4
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696200B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes