Triethylamine → HCID 178495797, compound

HRID 78441Notes

Reaction equation

HRID 78441 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C2C=CC=C(C(Cl)=O)C=2C=CC=1.[CH3:27][O:28][CH2:29][CH2:30][N:31]1[C:35]([CH3:36])=[C:34]([CH3:37])[S:33][C:32]1=[NH:38].CCN(CC)CC>C1COCC1>[CH3:27][O:28][CH2:29][CH2:30][N:31]1[C:35]([CH3:36])=[C:34]([CH3:37])[S:33]/[C:32]/1=[N:38]\[C:11]([C:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 232489Quinoline-5-carboxylic acidHCID 10241650Quinoline-5-carbonyl Chloride2×HCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495797HCID 178495797, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The quinoline-5-carboxylic acid (Lancaster, 0.25 g, 1.4 mmol) was converted to quinoline-5-carbonyl chloride using 5 mL SOCl2 using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and quinoline-5-carbonyl chloride in 30 mL THF were processed as in Example 134B to afford the title compound (0.18 g, 0.53 mmol, 49% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.30 (d, J=0.7 Hz, 3H), 2.34 (s, 3H), 3.31 (s, 3H), 3.80 (t, J=5.1 Hz, 2H), 4.49 (t, J=5.3 Hz, 2H), 7.60 (dd, J=8.6, 4.2 Hz, 1H), 7.83 (dd, J=8.5, 7.1 Hz, 1H), 8.15 (dt, J=8.5, 1.0 Hz, 1H), 8.40 (dd, J=7.3, 1.2 Hz, 1H), 8.87 (dd, J=4.1, 1.7 Hz, 1H), 9.55 (ddd, J=8.8, 1.7, 0.7 Hz, 1H); MS (DCI/NH3) m/z 342 (M+H)+; Anal. calculated for C18H19N3O2S: C, 63.32; H, 5.61; N, 12.31. Found: C, 63.44; H, 5.05; N, 12.10.

Sources & evidence

ORD record
ord-10e9472fe899444784ee5720520bb399
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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