Acetic Anhydride → N-{3-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-acetamide

HRID 8271Notes

Reaction equation

HRID 8271 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][NH2:29])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:32])[CH3:31])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 219925573-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propylamine

Product 1

HCID 10224393N-{3-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propylamine (25 mg, 0.06 mmol) in pyridine (1 mL) at room temperature is added acetic anhydride (500 μL, 5.3 mmol). The mixture is stirred for 2 h, concentrated in vacuo, and the residue chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide) to yield the title compound, 12 mg (47%), as a light brown solid

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-6984952448a0457eb09d4bff5fc92657
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

Loading…