Triethylamine → HCID 58975051, compound

HRID 737059Notes

Reaction equation

HRID 737059 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=CC=2N=N1.[C:28]1([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([S:43]([C:46]3[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][CH:47]=3)(=[O:45])=[O:44])[CH:35]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[O:55]1CCC(NC)[CH2:56]1.C(N(CC)CC)C>C(Cl)Cl>[C:28]1([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([S:43]([C:46]3[CH:47]=[CH:48][C:49]([C:50]([NH:8][CH2:12][CH:13]4[CH2:14][CH2:15][O:55][CH2:56]4)=[O:51])=[CH:53][CH:54]=3)(=[O:45])=[O:44])[CH:35]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 222257063-Furanamine, tetrahydro-N-methyl-HCID 589751414-(3-Phenyl-indole-1-sulfonyl)-benzoic acid

Product 1

HCID 58975051HCID 58975051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.0 mmol, 1.5 equiv) to a solution of 4-(3-phenyl-indole-1-sulfonyl)-benzoic acid (1.23 g, 3.26 mmol, 1 equiv), (tetrahydro-furan-3-yl)-methylamine (331 mg, 3.27 mmol, 1.0 equiv), and triethylamine (2.3 mL, 1.7 g, 17 mmol, 5.0 equiv) in anhydr CH2Cl2 (12 mL). After 1 h, rotary evaporate the reaction solution and transfer the resultant residue to a column of silica gel (235 mm×35 mm dia.) and elute (50-90% EtOAc/hex). This yields 486 mg (32.4%) of rac-4-(3-phenyl-indole-1-sulfonyl)-N-(tetrahydro-furan-3-ylmethyl)-benzamide as a yellow foam. MS (m/e): 460.96 (M+1); 459.04 (M−1).

Workup

  1. customrotary evaporate the reaction solution
  2. washelute (50-90% EtOAc/hex)

Sources & evidence

ORD record
ord-89df3f657bc645ce8f2dc3f05bc93065
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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