Triethylamine → HCID 70872696, compound

HRID 73017Notes

Reaction equation

HRID 73017 reaction equation
[CH2:1]([N:8]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[O:16][C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=1[CH3:39])([CH3:28])[CH3:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.C([O-])(O)=O.[Na+].CN(C=O)C>[CH2:1]([N:8]1[CH2:18][CH:17]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[O:16][C:10]2([CH2:11][CH2:12][N:13]([C:34]([C:33]3[CH:37]=[CH:38][C:30]([O:29][CH:26]([CH3:27])[CH3:28])=[C:31]([CH3:39])[CH:32]=3)=[O:35])[CH2:14][CH2:15]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592729354-Isopropoxy-3-methylbenzoic acidHCID 683107764-Benzyl-2-(p-tolyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Product 1

HCID 70872696HCID 70872696, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecane (100 mg, 0.30 mmol), 4-isopropoxy-3-methyl-benzoic acid (61 mg, 0.31 mmol) and HATU (119 mg, 0.31 mmol) was stirred in DCM (450 μL) and DMF (450 μL) for 5 minutes. Triethylamine (83 μL, 0.59 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with sat. aq. NaHCO3 (5 mL) and extracted with DCM (3×5 mL), dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel column chromatography (0-100% EtOAc/hexane) to give [8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone as a colorless oil (120 mg, 79%). ESI-MS m/z calc. 512.3. Found 513.3 (M+1)+; Retention time: 1.86 minutes (3 min run).

Workup

  1. extractionextracted with DCM (3×5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel column chromatography (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-64e2d3ec44624dfbbf8fa56207ec127f
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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