Hydrochloric Acid → HCID 69065668, compound

HRID 216158Notes

Reaction equation

HRID 216158 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[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:18]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=2)[N:16]=1.[ClH:38]>CCO.CCOCC>[ClH:38].[CH3:13][O:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:18]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=2)[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 53317523HCID 53317523, compound

Product 1

HCID 69065668HCID 69065668, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 2-pyridin-3-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-pyridin-3-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-pyridin-3-yl-ethyl)-amine hydrochloride [33.2 mg, 45%, Example 43(i)] as a solid. LC/MS: RT=1.53 minutes, MS: 337 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □8.82 (1H, s), 8.76 (1H, m), 8.43 (1H, m), 7.95 (1H, m), 7.32-7.45 (3H, m), 7.11 (1H, m), 6.64 (1H, s), 3.98 (3H, s), 3.79 (3H, s), 3.76 (2H, m), 3.09 (2H, m). IC50=248 nM

Sources & evidence

ORD record
ord-af13aefd6eda4153b30652a0a61f03dd
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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