Hydrochloric Acid → HCID 69073422, compound

HRID 216156

Reaction equation

HRID 216156 reaction equation
[N+](C1C=CC(CCN)=CC=1)([O-])=O.[CH3:13][O:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)[N:16]=1.[ClH:37]>CCO.CCOCC>[ClH:37].[CH3:13][O:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 57636084HCID 57636084, compound

Product 1

HCID 69073422HCID 69073422, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 2-thiophen-2-yl-ethylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared [2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-(2-thiophen-2-yl-ethyl)-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether affording [2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-(2-thiophen-2-yl-ethyl)-amine hydrochloride [33.7 mg, 45%, Example 43(e)] as a solid. LC/MS: RT=2.52 minutes MS: 342 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □7.32-7.5 (4H, m), 7.13 (1H, m), 6.96 (2H, m), 6.64 (1H, s), 4 (3H, s), 3.8 (3H, s), 3.7 (2H, m), 3.12 (2H, m). IC50=9.7 nM

Sources & evidence

ORD record
ord-3b58409dcdbe4d3886df3e116af456cd
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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