Triethylamine → HCID 178490657, compound

HRID 452941Notes

Reaction equation

HRID 452941 reaction equation
[CH:1]1([C:4]2[S:8][C:7](=[NH:9])[N:6]([CH2:10][CH:11]3[CH2:15][CH2:14][CH2:13][O:12]3)[N:5]=2)[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22](O)=[O:23].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22](/[N:9]=[C:7]1\[S:8][C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:5][N:6]\1[CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1)=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666982515-cyclopropyl-3-(tetrahydrofuran-2-ylmethyl)-1,3,4-thiadiazol-2(3H)-imine

Product 1

HCID 178490657HCID 178490657, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound from Example 2A (70 mg, 0.31 mmol), 5-chloro-2-methoxy-benzoic acid (64 mg, 0.34 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (185 mg, 0.46 mmol) and triethylamine (130 L, 0.93 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 12 hour. The mixture was diluted with water, and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with ethyl acetate/hexanes 2:3) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.95-1.01 (m, 2H) 1.14-1.21 (m, 2H) 1.67-1.78 (m, 1H) 1.79-1.93 (m, 2H) 1.91-2.00 (m, 1H) 2.30-2.39 (m, 1H) 3.65 (dd, J=13.81, 7.06 Hz, 1H) 3.77 (dd, J=13.50, 6.75 Hz, 1H) 3.80 (s, 3H) 4.21 (dd, J=13.20, 4.60 Hz, 1H) 4.31-4.38 (m, 1H) 4.43 (dd, J=12.89, 7.36 Hz, 1H) 7.13 (d, J=8.90 Hz, 1H) 7.49 (dd, J=8.90, 2.76 Hz, 1H) 7.73 (d, J=2.76 Hz, 1H); MS (ESI+) m/z 394 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, eluting with ethyl acetate/hexanes 2:3)

Sources & evidence

ORD record
ord-383bd1d5f8e84b9491de1a438d7a55dc
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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