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Triethylamine → HCID 483549, compound

HRID 260474
Notes
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Reaction equation

HRID 260474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[C:5]2[S:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[N:34]1[CH:35]=[CH:36][C:31]([CH2:30][NH:29][C:11]([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[S:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:13])=[CH:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22401517HCID 22401517, compound

Product 1

HCID 483549HCID 483549, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a mixture of 5-chloro-3-phenylsulfinylindole-2-carboxylic acid (0.096 g, 0.3 mmol), triethylamine (0.061 g, 0.6 mmol), 4-aminomethylpyridine (0.043 g, 0.4 mmol) in dry dimethylformamide was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) (0.155 g, 0.35 mmol). The mixture was stirred at room temperature under nitrogen for three days. Following evaporation, the residue was partitioned between ethyl acetate and water. The ethyl acetate phase was separated and washed with dilute hydrochloric acid. The acidic extract was neutralized with aqueous sodium bicarbonate and the product extracted into ethyl acetate. The ethyl acetate extract was washed well with aqueous sodium bicarbonate, then brine, and dried over magnesium sulfate. Evaporation afforded a solid residue which was recrystallized from ethyl acetate to give the title compound, mp 233°-235° C. Anal. Calcd for C21H16ClN3O2S: C, 61.54; H, 3.93; N, 10.25. Found: C, 61.39; H, 3.95; N, 10.36. NMR (DMSO-d6) δ9.62 (1H, t, J=6 Hz), 8.53 (2H, d, J=6 Hz), 7.80 (1H, d, J=2 Hz), 7.67 (2H, m), 7.64 (2H, d, J=9 Hz), 7.44-7.54 (3H, m), 7.33 (3H, m), 4.60 (2H, dq, J=9, 6 Hz).

Workup

  1. customevaporation
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate phase was separated
  4. washwashed with dilute hydrochloric acid
  5. extractionThe acidic extract
  6. extractionthe product extracted into ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed well with aqueous sodium bicarbonate
  9. dry with materialbrine, and dried over magnesium sulfate
  10. customEvaporation
  11. customafforded a solid residue which
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a2911711d3fb47bb869a0448ad4991d7
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05527819

Reaction notes

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