Dimethylamine → HCID 23533341, compound

HRID 1795341Notes

Reaction equation

HRID 1795341 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, compound

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
  5. custommethanol afforded the clean product (0.142 g; 92%)

Sources & evidence

ORD record
ord-fa54ba1731204a64955579b4488a248b
Source dataset
uspto-grants-2006_04
Patent number
US07026314B2

Reaction notes

Loading…