Triethylamine → N-(3-pyridylmethyl)-5-chloro-3-phenylthioindole-2-carboxamide

HRID 260460Notes

Reaction equation

HRID 260460 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38](O)=[S:39])=[C:32]2[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[NH2:47][CH2:48][C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1.C(N(CC)CC)C>CN(C)C=O>[N:51]1[CH:52]=[CH:53][CH:54]=[C:49]([CH2:48][NH:47][C:38]([C:33]2[NH:34][C:35]3[C:31]([C:32]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:30][C:29]([Cl:28])=[CH:37][CH:36]=3)=[S:39])[CH:50]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178526153HCID 178526153, compound

Product 1

HCID 86749574N-(3-pyridylmethyl)-5-chloro-3-phenylthioindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorphosphate (0.73 g, 1.6 mmol) was added to a solution of 5-chloro-3-phenylthio-indole-2-carboxylic acid (0.50 g, 1.6 mmol), 3-aminomethylpyridine (0.35 g, 3.2 mmol) and triethylamine (0.50 mL, 3.2 mmol) in degassed dimethylformamide (25 mL). The reaction was stirred at room temperature overnight. The precipitated product was filtered and the filter cake washed well with water. The solid was triturated with 30% ethyl acetate in hexane, filtered and dried at 60° C. in vacuo for 72 h. The title compound was obtained as an off-white solid, mp 240°-241° C. Anal. Calc. for C21H16ClN3OS.0.25 H2O: C, 63.31; H, 4.17; N, 10.54. Found: C, 63.34; H, 4.06; N, 10.71. NMR (DMSO-d6): δ12.54 (1H, s), 8.91 (1H, t, J=6 Hz), 8.51 (1H, s), 8.42 (1H, d, J=5 Hz), 7.58 (2H, m), 7.45 (1H, m), 7.25 (4H, m), 7.15 (1H, t, J=7 Hz), 7.04 (2H, d, J=8 Hz), 4.58 (2H, d, J=6 Hz).

Workup

  1. filtrationThe precipitated product was filtered
  2. washthe filter cake washed well with water
  3. customThe solid was triturated with 30% ethyl acetate in hexane
  4. filtrationfiltered
  5. customdried at 60° C. in vacuo for 72 h

Sources & evidence

ORD record
ord-5d27dcdc32c1461fa49b63fa50397c40
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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