Triethylamine → HCID 58975123, compound

HRID 737053Notes

Reaction equation

HRID 737053 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:15][C:16]1([F:42])[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([S:30]([C:33]3[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:22]=2)[CH2:17]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>C(Cl)Cl>[F:42][C:16]1([F:15])[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([C:37]([NH:7][CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[O:38])=[CH:40][CH:41]=3)(=[O:32])=[O:31])[CH:22]=2)[CH2:17]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4192234-AminotetrahydropyranHCID 58975084HCID 58975084, compound

Product 1

HCID 58975123HCID 58975123, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a 2 ml CH2Cl2 solution of Tetrahydro-pyran-4-ylamine (62 mg, 0.0610 mmol, 1.1 eq) and triethylamine (365 mg, 3.6 mmol, 6.5 eq) to a 2 ml CH2Cl2 solution of 4-[3-(3,3-Difluoro-cyclopentyl)-indole-1-sulfonyl]-benzoic acid. Add benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (245 mg, 0.555 mmol, 1.0 eq) and stir reaction at room temperature for 18 hours. Remove volatiles on rotovap and purify by silica gel chromatography, followed by SCX ionic chromatography to give 4-[3-(3,3-Difluoro-cyclopentyl)-indole-1-sulfonyl]-N-(tetrahydro-pyran-4-yl)-benzamide (240 mg, 89% yield). Mass Spectrum (m/e): 489.71 (MH+).

Workup

  1. customreaction at room temperature for 18 hours
  2. customRemove volatiles on rotovap and purify by silica gel chromatography

Sources & evidence

ORD record
ord-b414428c5ef74f548f2bde46d6881e53
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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