Triethylamine → HCID 86603032, compound

HRID 735485Notes

Reaction equation

HRID 735485 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:32]=[CH:31][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:33]([F:36])([F:35])[F:34])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:50][O:51][NH:52][CH3:53].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:8]1[C:16]([C:17]2[CH:32]=[CH:31][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([N:52]([O:51][CH3:50])[CH3:53])=[O:27])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:33]([F:35])([F:34])[F:36])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11511476HCID 11511476, compound

Product 1

HCID 86603032HCID 86603032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of 3-{4-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}benzoic acid (115.8 mg, 0.237 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (86 mg, 0.356 mmol), O,N-dimethyl-hydroxylamine hydrochloride (69 mg, 0.711 mmol) and 0.3 mL of triethylamine dissolved in 2 mL CH2Cl2 was stirred at room temperature overnight. The reaction mixture was quenched with 1M HCl(aq) and the crude material was extracted with CH2Cl2. The crude material was purified with flash chromatography using EtOAc/heptane, 3:7, as eluent to afford 17 mg of analytically pure product.

Workup

  1. customThe reaction mixture was quenched with 1M HCl(aq)
  2. extractionthe crude material was extracted with CH2Cl2
  3. customThe crude material was purified with flash chromatography
  4. customas eluent to afford 17 mg of analytically pure product

Sources & evidence

ORD record
ord-9b74ccbc884c4fa9a8c61dc2121263a0
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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