Triethylamine → HCID 73335727, compound

HRID 710644Notes

Reaction equation

HRID 710644 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[F:17][C:18]([F:31])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:27](=[O:28])[CH2:26][C:23]4[CH:24]=[CH:25][C:20]([O:19][C:18]([F:30])([F:17])[F:31])=[CH:21][CH:22]=4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73335727HCID 73335727, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.023 g, 0.10 mmol), 4-(trifluoromethoxy)phenylacetic acid (0.025 g, 0.11 mmol) and Et3N (0.060 mL, 0.43 mmol) in DMF (0.6 mL) was added HATU (0.060 g, 0.15 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.040 g, 95%). 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1H), 7.43 (m, 2H), 7.30 (m, 2H), 7.18 (m, 4H), 3.91 (s, 2H), 3.76 (m, 2H), 2.79 (t, J=6.4 Hz, 2H), 2.00 (m, 2H); MS: (ES) m/z calculated for C21H17F4N3O2 [M+H]+ 420.1, found 420.1.

Workup

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-c903bd84c77f4d75b2f8d577b6579a75
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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