Ethyl 4-butyrylbenzoate → Ethyl 4-(1-((6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl)amino)butyl)benzoate

HRID 1520962Notes

Reaction equation

HRID 1520962 reaction equation
[C:1]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4].[CH:17]1([C:20]2[CH:21]=[N:22][N:23]([C:25]3[N:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)[CH:24]=2)[CH2:19][CH2:18]1.[B][B][B][B][B][B][B][B][B][B]>CO>[CH:17]1([C:20]2[CH:21]=[N:22][N:23]([C:25]3[N:30]=[CH:29][C:28]([NH:31][CH:1]([C:6]4[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=4)[CH2:2][CH2:3][CH3:4])=[CH:27][CH:26]=3)[CH:24]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 67980577Ethyl 4-butyrylbenzoateHCID 681567276-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amineHCID 178419135HCID 178419135, compound

Product 1

HCID 86669097Ethyl 4-(1-((6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl)amino)butyl)benzoateYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-butyrylbenzoate (121 mg, 0.549 mmol) and 6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amine (0.110 g, 0.549 mmol) in methanol (1.3 ml) was added decaborane (27 mg, 0.22 mmol). The reaction was stirred for 12 hours at ambient temperature. The reaction mixture was quenched with aqueous 1.0M hydrochloric acid and concentrated in vacuo. The crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane) to yield the product (26 mg, 12%) as an oil. 1H NMR (400 MHz, CDCl3): δ 8.05 (s, 1H), 8.01 (d, J=8.2 Hz, 2H), 7.67 (br. s., 1H), 7.62 (d, J=9.0 Hz, 1H), 7.44 (s, 1H), 7.40 (d, J=8.2 Hz, 2H), 6.90 (d, J=6.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 3H), 1.76-1.90 (m, 2H), 1.72 (tt, J=8.4, 5.1 Hz, 1H), 1.41-1.52 (m, 2H), 1.38 (t, J=7.1 Hz, 3H), 0.96 (t, J=7.3 Hz, 3H), 0.86 (ddd, J=8.2, 5.9, 3.9 Hz, 2H), 0.56 (dt, J=5.9, 4.1 Hz, 2H).

Workup

  1. customThe reaction mixture was quenched with aqueous 1.0M hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-003062f379b140928718067808e5757c
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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