Quinoline-3-carboxylic acid → HCID 45268070, compound

HRID 574311Notes

Reaction equation

HRID 574311 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]2[CH2:19][CH2:18][C:17]3[C:16]([OH:20])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([C:34](O)=[O:35])[CH:25]=1>>[OH:20][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH2:18][CH2:19][CH:10]([N:9]([CH2:21][CH2:22][CH3:23])[CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][N:4]([C:34]([C:26]3[CH:25]=[N:24][C:33]4[C:28]([CH:27]=3)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:35])[CH2:3][CH2:2]1)[CH2:11]2

Participants

3

Reactant 2

HCID 80971Quinoline-3-carboxylic acidHCID 60167428HCID 60167428, compound

Product 1

HCID 45268070HCID 45268070, compoundYield 99.9%

Procedure

Compound 40j was prepared following Procedure G using 39b (172 mg, 0.542 mmol) and quinoline-3-carboxylic acid (112 mg, 0.650 mmol) to give 40j (256 mg, 85%) after column chromatography. 1H NMR (400 MHz, CD3OD) 0.93-0.96 (t, 3H, J=7.2 Hz), 1.57-1.59 (m, 3H), 2.18 (m, 2H), 2.55-3.00 (m, 14H), 3.55 (bs, 2H), 3.85 (bs, 2H), 6.53-6.58 (t, 2H, J=8 Hz), 6.88-6.91 (t, 1H, J=11.2 Hz), 7.81-7.72 (t, 1H, J=7.6 Hz), 7.85-7.88 (t, 1H, J=7.6 Hz), 8.03-8.1 (m, 2H), 8.45 (bs, 1H), 8.89 (bs, 1H). The free base of 40j was converted into its HCl salt. m.p. 142-146° C. Anal. [C29H36N4O2.3HCl.2H2O] C, H, N.

Workup

  1. customCompound 40j was prepared

Sources & evidence

ORD record
ord-91878a0ac6e24ed7b98af45f8f596a2a
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

Loading…