Triethylamine → HCID 73335730, compound

HRID 710647Notes

Reaction equation

HRID 710647 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([OH:10])=O)[CH:6]=1.C(Cl)(C(Cl)=O)=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1.CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([N:28]2[CH2:29][CH2:30][CH2:31][C:32]3[N:24]([C:21]4[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=4)[N:25]=[CH:26][C:27]2=3)=[O:10])[CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 6485340(4-Chloro-pyrazol-1-yl)-acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73335730HCID 73335730, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[(4-chloro-pyrazol-1-yl)]acetic acid (0.050 g, 0.31 mmol), (COCl)2 (0.060 mL, 0.70 mmol) and DMF (1 drop) in CH2Cl2 (1 mL) was stirred for 30 min at rt. It was then evaporated to dryness on a high vacuum pump. The obtained oil was added to a mixture containing 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.020 g, 0.092 mmol) and NEt3 (0.070 mL, 0.50 mmol) in CH2Cl2 (1 mL). The resulting mixture was then 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 (0.012 g, 36%). 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.60 (s, 1H), 7.51 (s, 1H), 7.44 (dd, J=8.8, 4.6 Hz, 2H), 7.17 (dd, J=9.2, 8.8 Hz, 2H), 5.16 (s, 2H), 3.82 (m, 2H), 2.85 (t, J=6.2 Hz, 2H), 2.09 (m, 2H); MS: (ES) m/z calculated for C17H15ClFN5O [M+H]+ 360.1, found 360.1.

Workup

  1. customIt was then evaporated to dryness on a high vacuum pump
  2. additionThe obtained oil was added to a mixture
  3. stirringThe resulting mixture was then stirred at rt for 30 min
  4. customIt was then quenched with water
  5. custompartitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d91ed65727cb428fa7e3fd97dc52fe14
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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