Pyrrolidine → HCID 89781942, compound

HRID 1055983Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=[CH:7]2.C(Cl)(=O)C(Cl)=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:14])[CH:8]=[CH:7]2

Participants

Reactant 3

HCID 31268Pyrrolidine

HCID 65578Oxalyl chloride

HCID 336959058-Bromoquinoline-2-carboxylic acid

Product 1

HCID 89781942HCID 89781942, compoundYield 94.2%

Procedure

This compound (365 mg, 94% yield) as a tan crystalline solid was prepared similarly to that described in Example 167a, using 8-bromoquinoline-2-carboxylic acid (Princeton BioMolecular Research, Monmouth Junction, N.J.; 320 mg, 1.27 mmol), oxalyl chloride (2.54 mmol), and pyrrolidine (0.10 mL, 1.27 mmol) as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (1H, d, J=8.4 Hz), 8.23 (1H, dd, J=7.6, 1.2 Hz), 8.11 (1H, dd, J=8.2, 1.0 Hz), 8.01 (1H, d, J=8.6 Hz), 7.63 (1H, t, J=7.8 Hz), 3.98 (2H, t, J=6.5 Hz), 3.61 (2H, t, J=6.5 Hz), 1.95 (4H, m). m/z (ESI, +ve) 307/307 (M+H)+.

Sources & evidence

ORD record: ord-7f1e2f8f7b7842b683f410edeb812bb5
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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