Triethylamine → HCID 68290983, compound

HRID 73010Notes

Reaction equation

HRID 73010 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:11][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][C:30]=1[CH3:38])([CH3:27])[CH3:26].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.CN(C=O)C>[CH2:1]([N:8]1[CH2:13][C:12]2([CH2:18][CH2:17][N:16]([C:33]([C:32]3[CH:36]=[CH:37][C:29]([O:28][CH:25]([CH3:26])[CH3:27])=[C:30]([CH3:38])[CH:31]=3)=[O:34])[CH2:15][CH2:14]2)[O:11][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

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 682909524-Benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane

Product 1

HCID 68290983HCID 68290983, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane (222 mg, 0.69 mmol), 4-isopropoxy-3-methyl-benzoic acid (140 mg, 0.72 mmol) and HATU (262 mg, 0.69 mmol) was stirred in a mixture of DCM (1 mL) and DMF (1 mL) for 5 minutes. Triethylamine (192 μL, 1.38 mmol) was added and the reaction mixture was stirred for 16 hours, then concentrated in vacuo, diluted with sat. aq. NaHCO3, extracted with ethyl acetate (3×2 mL), dried over MgSO4, filtered and concentrated in vacuo and purified by silica gel column chromatography using 0-60% EtOAc/DCM as eluent to give (10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (343 mg, 100%) as a yellow oil. ESI-MS m/z calc. 406.5. Found 407.7 (M+1)+; Retention time: 1.13 minutes (3 min run).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with sat. aq. NaHCO3
  3. extractionextracted with ethyl acetate (3×2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-f8b1bb95faa54dd0b5a4dd16511841d0
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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