Hydrochloric Acid → HCID 68575137, compound

HRID 40802Notes

Reaction equation

HRID 40802 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1.[ClH:27]>CO>[ClH:24].[ClH:27].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25262923HCID 25262923, compound

Product 1

HCID 68575137HCID 68575137, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,4-diamino-6-ethyl-5-(3-(6-chloroquinolin-4-yloxy)propoxy)pyrimidine (0.5608 g, 1.5 mmol) in methanol (1 mL) was added two equivalents of concentrated HCl. The titled compound was obtained, after trituration of the reaction mixture with diethyl ether, as a off-white crystalline solid (0.6366 g, 95%). 1H NMR (500 MHz, DMSO-d6): 1.09 (3H, t, J=7.7 Hz), 2.43 (2H, m), 2.48 (2H, m), 3.99 (2H, t, J=6.2 Hz), 4.70 (2H, t, J=5.9 Hz), 7.55 (2H, bs), 7.64 (1H, d, J=6.6 Hz), 7.95 (1H, s), 3.15 (1H, dd, J=9.1, 2.4 Hz), 8.37 (2H, m), 8.41 (1H, d, J=9.1 Hz), 9.22 (1H, d, J=6.5 Hz), 12.80 (1H, s).

Sources & evidence

ORD record
ord-8dcd056e31bd4ac1ba5b996f8f41044d
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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