Triethylamine → HCID 178490720, compound

HRID 2235130Notes

Reaction equation

HRID 2235130 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:30]=[C:29]3[C:25]([CH2:26][CH2:27][N:28]3[S:31]([C:34]3[CH:39]=[C:38](Cl)[CH:37]=[CH:36][C:35]=3[O:41][CH3:42])(=[O:33])=[O:32])=[CH:24][CH:23]=2)=[O:21])=[CH:15][CH:14]=1)#[N:12]>CS(C)=O.O>[OH:3][NH:2][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:30]=[C:29]3[C:25]([CH2:26][CH2:27][N:28]3[S:31]([C:34]3[CH:39]=[C:38]([Cl:1])[CH:37]=[CH:36][C:35]=3[O:41][CH3:42])(=[O:33])=[O:32])=[CH:24][CH:23]=2)=[O:21])=[CH:15][CH:14]=1)=[NH:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 866113241-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide

Product 1

HCID 178490720HCID 178490720, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of hydroxylamine hydrochloride (223 mg, 3.21 mmol, 5 equiv.) in dimethyl sulfoxide (3 ml) was treated with triethylamine (0.45 ml, 3.21 mmol, 5 equiv.) and stirred at room temperature for 5 min. The white precipitate was filtered off and to the filtrate, 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide (300 mg, 0.64 mmol, 1 equiv.) (prepared as illustrated in example 37, steps 1 to 3) was added. The mixture was stirred at 75° C. for 1 hour and 15 min. The reaction mixture was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic phase was extracted three times with 0.5 N HCl. The combined aqueous phase was adjusted to pH 9-10 with NaOH 1N and extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4 and the solvent was evaporated. Crude 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide was obtained as a white solid, 261 mg (81%), which was used as such in the following reaction. MS (ISP): m/e=501.3 (M+H+.), δH (300 MHz; d6-DMSO) 10.25 (1H, s), 9.50 (1H, s), 7.80 (1H, s), 7.55-7.71 (7H, m), 7.28 (1H, d), 7.16 (1H, d), 5.69 (2H, s), 4.04 (2H, t), 3.60 (3H, s), 3.06 (2H, t).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 75° C. for 1 hour and 15 min
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. extractionThe organic phase was extracted three times with 0.5 N HCl
  6. extractionextracted three times with ethyl acetate
  7. dry with materialThe combined organic phases were dried with Na2SO4
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f38d2959141b481c91c663ce9a21de1f
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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