Hydrochloric Acid → HCID 68574377, compound

HRID 40828Notes

Reaction equation

HRID 40828 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]([O:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=3)[N:17]=[C:16]([CH3:33])[CH:15]=2)=[C:4]([CH2:34][CH3:35])[N:3]=1.[ClH:36]>C(O)C>[ClH:36].[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]([O:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=3)[N:17]=[C:16]([CH3:33])[CH:15]=2)=[C:4]([CH2:34][CH3:35])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 252629252,4-Diamino-6-ethyl-5-(3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine

Product 1

HCID 68574377HCID 68574377, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring suspension of 2,4-diamino-6-ethyl-5-(3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine obtained from step (c) (0.179 g, 0.37 mmol) in ethanol (0.5 mL) was added one equivalent of hydrochloric acid at 25° C. After evaporation of solvent and trituration with acetone, the product was obtained as white crystalline solid (0.117 g, 61%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.5 Hz), 1.15 (3H, t, J=7.0 Hz), 2.00 (2H, m), 2.35 (4H, m), 2.40 (2H, m), 2.70 (3H, s), 3.85 (2H, t, J=6.0 Hz), 4.02 (2H, q, J=7.0 Hz), 4.10 (2H, t, J=6.0 Hz), 4.52 (2H, m), 7.25 (s, 1H), 7.42 (3H, m), 7.90 (1H, bs), 8.00 (1H, d, J=10 Hz), 8.30 (1H, bs).

Workup

  1. customAfter evaporation of solvent and trituration with acetone

Sources & evidence

ORD record
ord-9801fed58ad544d19abeffa7dd02a2cd
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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