Dimethylamine → HCID 23533341, compound

HRID 1825660Notes

Reaction equation

HRID 1825660 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:25]=[C:24](Cl)[C:23]4[C:18](=[C:19]([Br:29])[CH:20]=[C:21]([O:27][CH3:28])[CH:22]=4)[N:17]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:30][NH:31][CH3:32]>O1CCCC1>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:25]=[C:24]([N:31]([CH3:32])[CH3:30])[C:23]4[C:18](=[C:19]([Br:29])[CH:20]=[C:21]([O:27][CH3:28])[CH:22]=4)[N:17]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86587188HCID 86587188, compound

Product 1

HCID 23533341HCID 23533341, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-bromo-4-chloro-6-methoxy-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide (Reference Example 28a) (0.1512 g, 0.317 mmol) in 100 mL 2.0 M dimethyl amine in tetrahydrofuran was heated at 100° C. in a Parr bomb. The initial pressure was 75-80 psi and then remained at approximately 60 psi. After 18 hours, the reaction was cooled to room temperature, concentrated and dried to afford the crude product as a brown solid. Purification on silica gel using a gradient of 100:0 to 95:5 methylene chloride:methanol afforded the clean product (0.142 g, 92%). 1H NMR (300 MHz, DMSO, d6) δ 10.20 (s, 1 H, C(O)NH), 7.90 (d, 1 H, Jm=2.7 Hz, ArH5), 7.69 (d, 2 H, Jo=9.0 Hz, ArH2′& H6′), 7.60 (s, 1 H, ArH3), 7.41 (d, 1 H, Jm=2.7 Hz, ArH7), 7.01 (d, 2 H, Jo=9.0 Hz, ArH3′& H5′), 3.96 (s, 3 H, OCH3), 3.75 (t, 4 H, J=4.8 Hz, OCH2CH2N), 3.10 (t, 4 H, J=4.8 Hz, OCH2CH2N), 3.08 (s, 6 H, N(CH3)2); Mass Spec.: calc. for [C21H19BrClN3O3+H]+ Theor. m/z=485, 487; Obs.=485, 487

Workup

  1. concentrationconcentrated
  2. customdried
  3. customto afford the crude product as a brown solid
  4. customPurification on silica gel using a gradient of 100:0 to 95:5 methylene chloride

Sources & evidence

ORD record
ord-f622091b54334d4fbc3d7934f1e7880a
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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