2-Chloroquinoline → HCID 69059190, compound

HRID 227613Notes

Reaction equation

HRID 227613 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][C:3]=1[O:19][CH3:20].Cl[C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1>>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)=[C:3]([O:19][CH3:20])[CH:4]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 119282-ChloroquinolineHCID 69055425HCID 69055425, compound

Product 1

HCID 69059190HCID 69059190, compoundYield 5%

Procedure

A mixture of Example 70A (100 mg, 0.35 mmol) and 2-chloroquinoline (62 mg, 0.38 mmol) was heated to 200° C. under nitrogen for 20 minutes, cooled to room temperature, and partitioned between saturated NaHCO3 and dichloromethane. The aqueous phase was extracted three times with dichloromethane and the combined organic extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was triturated with diethyl ether to provide 6 mg (5%) of the desired product. MS(ESI(+)) m/e 414 (M+H)+; 1H NMR (DMSO-d6) δ 9.08 (d, 1H, J=8.2 Hz); 8.70 (s, 1H); 8.28 (s, 1H); 8.08 (d, 1H, J=8.8 Hz); 7.73 (t, 2H, J=8.8 Hz); 7.61-7.56 (m, 1H); 7.44 (d, 1H, J=9.1 Hz); 7.34-7.29 (m, 1H); 7.06 (d, 1H, J=2.0 Hz); 7.02-6.99 (m, 1H); 3.93 (s, 3H); 2.37 (s, 3H).

Workup

  1. custompartitioned between saturated NaHCO3 and dichloromethane
  2. extractionThe aqueous phase was extracted three times with dichloromethane
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was triturated with diethyl ether

Sources & evidence

ORD record
ord-a55db44a87c0443a93a80d84fc0f4983
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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