Hydrochloric Acid → HCID 69064091, compound

HRID 216161Notes

Reaction equation

HRID 216161 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][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[N:16]=1.[ClH:39]>CCO.CCOCC>[ClH:39].[CH3:13][O:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 53321836HCID 53321836, compound

Product 1

HCID 69064091HCID 69064091, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 3-phenyl-propylamine 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]-(3-phenyl-propyl)-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]-(3-phenyl-propyl)-amine hydrochloride [60.6 mg, 79%, Example 43(l)] as a solid. LC/MS: RT=2.65 minutes, MS: 350 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □7.1-7.5 (9H, m), 6.62 (1H, s), 3.95 (3H, s), 3.8 (3H, s), 3.42 (2H, m), 2.64 (2H, m), 1.88 (2H, m). IC50=1686 nM

Sources & evidence

ORD record
ord-109409cb87b3421c973c6525f70a0886
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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