Diisopropylethylamine → HCID 68311128, compound

HRID 73009Notes

Reaction equation

HRID 73009 reaction equation
[C:1]1([CH:7]2[O:17][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][N:9]([CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:23]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][C:28]=1[CH3:36])([CH3:25])[CH3:24].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:23]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:14]2[CH2:15][CH2:16][C:11]3([O:17][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:8][N:9]([CH2:18][C:19]([F:21])([F:22])[F:20])[CH2:10]3)[CH2:12][CH2:13]2)=[O:32])=[CH:29][C:28]=1[CH3:36])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 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 6831077510-Phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane

Product 1

HCID 68311128HCID 68311128, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane (hydrochloride salt) (150 mg, 0.39 mmol) and 4-isopropoxy-3-methyl-benzoic acid (75 mg, 0.39 mmol) in DMF (1 mL) was added at room temperature O—(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (162 mg, 0.43 mmol) and diisopropylethylamine (337 μL, 1.94 mmol) and reaction mixture was stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate and washed with 1M NaOH and then brine solution. The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography using 10-60% EtOAc/hexane to give the desired compound as a white foam (147 mg, 73%) ESI-MS m/z calc. 490.2. Found 491.4 (M+1)+; Retention time: 2.42 minutes (3 min run).

Workup

  1. washwashed with 1M NaOH
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed202ad4377a478085ba468ed67067f9
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

Loading…