Triethylamine → HCID 21833747, compound

HRID 1741123Notes

Reaction equation

HRID 1741123 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][NH:37][C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:26][CH2:25]1.C(N(CC)CC)C>>[CH3:23][N:24]1[CH2:25][CH2:26][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][N:37]([C:20]([C:17]5[CH:18]=[CH:19][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[N:12]([CH3:13])[CH:11]=[N:10][CH:9]=7)=[CH:7][C:2]=6[CH3:1])=[CH:15][CH:16]=5)=[O:21])[C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:28][CH2:29]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]HCID 21833754HCID 21833754, compound

Product 1

HCID 21833747HCID 21833747, compoundYield 38.6%

Procedure

2'-Methyl-4'-(1-methylimidazol-5-yl)biphenyl-4-carboxylic acid (D93, 300 mg, 1.0 mmol) was heated at reflux in thionyl (15 ml) for 1 hour, cooled and evaporated in vacuo. The residue was redissolved in dry THF (10 ml) and treated with 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (D8, 250 mg, 1.0 mmol) and triethylamine (143 ul, 1.0 mmol) then stirred for 18 hours. The reaction mixture was evaporated in vacuo, partitioned between water and CHCl3 (3 times) and the organic extracts combined. The organics were dried over Na2SO4 and evaporated in vacuo to an orange gum. The gum was purified by flash silica gel chromatography (eluting with 3% MeOH/CHCl3) to yield the title compound as a pale yellow gum (200 mg, 38%) which was converted to the hydrochloride salt.

Workup

  1. temperatureat reflux in thionyl (15 ml) for 1 hour
  2. temperaturecooled
  3. customevaporated in vacuo
  4. dissolutionThe residue was redissolved in dry THF (10 ml)
  5. customThe reaction mixture was evaporated in vacuo
  6. custompartitioned between water and CHCl3 (3 times)
  7. dry with materialThe organics were dried over Na2SO4
  8. customevaporated in vacuo to an orange gum
  9. customThe gum was purified by flash silica gel chromatography (eluting with 3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-89e5f28b8b4446f487269a1d6e5f4947
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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