Hydrochloric Acid → HCID 69066223, compound

HRID 2110685Notes

Reaction equation

HRID 2110685 reaction equation
[N+](C1C=CC(CCN)=CC=1)([O-])=O.[CH3:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)[N:30]=[C:29]([O:41][CH3:42])[N:28]=3)=[CH:20][NH:21]2)=[CH:17][CH:16]=1.[ClH:43]>CCO.CCOCC>[ClH:43].[CH3:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)[N:30]=[C:29]([O:41][CH3:42])[N:28]=3)=[CH:20][NH:21]2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 53317887HCID 53317887, compound

Product 1

HCID 69066223HCID 69066223, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 2-(6-methoxy-1H-indol-3-yl)-ethylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared [2-(6-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether affording [2-(6-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [58.6 mg, 66%, Example 43(g)] as a solid. LC/MS: RT=2.48 minutes MS: 405 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □10.6 (1H, s), 7.3-7.5 (4H, m), 7.12 (1H, m), 7.02 (1H, m), 6.8 (1H, s), 6.61 (2H, m), 3.99 (3H, s), 3.8 (3H, s), 3.72 (3H, s), 3.58 (2H, m), 2.94 (2H, m). IC50=104 nM

Sources & evidence

ORD record
ord-40eb098360874e2ea43205c41cf55c14
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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