Triethylamine → 2-(1,3-benzoxazol-2-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

HRID 710661Notes

Reaction equation

HRID 710661 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.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[CH2:26][C:27](O)=[O:28].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>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[CH2:26][C:27]([N:12]1[CH2:13][CH2:14][CH2:15][C:16]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=[CH:10][C:11]1=2)=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 954457(1,3-Benzoxazol-2-yl)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 733359152-(1,3-benzoxazol-2-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanoneYield 53.1%

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, 0.11 mmol), benzooxazol-2-yl-acetic acid (0.023 g, 0.13 mmol) and NEt3 (0.060 mL, 0.43 mmol) in DMF (0.6 mL) was added HATU (0.050 g, 0.13 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between IPA/CHCl3 (1:2, 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 (0.022 g, 53%). 1H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 7.71 (m, 1H), 7.53 (m, 1H), 7.45 (dd, J=8.8, 4.8 Hz, 2H), 7.34 (m, 2H), 7.15 (dd, J=8.8, 8.4 Hz, 2H), 4.25 (s, 2H), 3.88 (m, 2H), 2.83 (t, J=6.4 Hz, 2H), 2.08 (m, 2H); MS: (ES) m/z calculated for C21H17FN4O2 [M+H]+ 377.1, found 377.1.

Workup

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between IPA/CHCl3 (1:2, 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-5975cbeb474b48f9b10c570d321afd97
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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