Water → HCID 136507783, compound

HRID 530028Notes

Reaction equation

HRID 530028 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][C:9](OCC)=[O:10])[N:5]=[C:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:3]=1[C:20]#[N:21].[Li]CCCC.O>C1COCC1>[O:10]=[C:9]1[CH2:8][CH2:7][N:6]2[N:5]=[C:4]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:3]([C:20]#[N:21])=[C:2]2[NH:1]1

Participants

5

Reactant 3

HCID 962WaterHCID 89462935HCID 89462935, compoundHCID 178418339Butyllithium

Product 1

HCID 136507783HCID 136507783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of ethyl 3-(5-amino-4-cyano-3-(pyridine-3-yl)-1H-pyrazol-1-yl)propanoate (213 mg, 0.75 mmol) in THF (5 mL) was added n-BuLi (0.6 mL, 1.49 mmol) at −60° C. The resulting mixture was stirred at −60° C. for 3 hours. 2 mL of water was added to quench the reaction and the THF was removed in vacuo. The residue was purified by HPLC to afford the desired product: MS (m/z): 240.1 [M+H]+, 1H NMR (DMSO, 400 MHz): δ11.79 (s, 1 H), 8.99 (s, 1 H), 8.65 (d, 1 H, J=5.2 Hz), 8.17 (d, 1 H, J=8.4 Hz), 7.57 (dd, 1 H, J=8.4 Hz, J=5.2 Hz), 4.38 (t, 2 H, J=7.6 Hz), 2.89 (t, 2 H, J=7.6 Hz).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe THF was removed in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-f784949c81864d10ba6162f5c945b737
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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