Triethylamine → HCID 73335729, compound

HRID 710645Notes

Reaction equation

HRID 710645 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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](O)=[O:26])=[CH:20][C:19]=1[O:28][C:29]([F:32])([F:31])[F:30].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>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([N:12]2[CH2:13][CH2:14][CH2:15][C:16]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:9]=[CH:10][C:11]2=3)=[O:26])=[CH:20][C:19]=1[O:28][C:29]([F:30])([F:32])[F:31]

Participants

6

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 17750699[4-Chloro-3-(trifluoromethoxy)phenyl]acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73335729HCID 73335729, compoundYield 85.9%

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-chloro-3-(trifluoromethoxy)phenylacetic acid (0.025 g, 0.10 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 and 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 (0.039 g, 85%). 1H NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 7.44 (m, 3H), 7.12-7.22 (m, 4H), 3.90 (s, 2H), 3.76 (m, 2H), 2.80 (t, J=6.2 Hz, 2H), 2.02 (m, 2H); MS: (ES) m/z calculated for C21H16ClF4N3O2 [M+H]+ 454.1, found 454.1.

Workup

  1. customIt was then quenched with water
  2. custompartitioned 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-68c48315809c4c49b33e9089a4656694
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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