Hydrochloric Acid → HCID 69065690, compound

HRID 2110686Notes

Reaction equation

HRID 2110686 reaction equation
[N+](C1C=CC(CCN)=CC=1)([O-])=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH2:25][NH:26][C:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=2)[N:30]=[C:29]([O:41][CH3:42])[N:28]=1.[ClH:43]>CCO.CCOCC>[ClH:43].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH2:25][NH:26][C:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=2)[N:30]=[C:29]([O:41][CH3:42])[N:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 57636101HCID 57636101, compound

Product 1

HCID 69065690HCID 69065690, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 2-(5-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-(5-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-(5-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [52.1 mg, 59%, Example 43(h)] as a solid. LC/MS: RT=2.45 minutes, MS: 405 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □10.65 (1H, s), 7.41 (1H, m), 7.36 (2H, m), 7.2 (1H, m), 7.13 (2H, m), 7.01 (1H, m), 6.7 (1H, dd, J=9.6, 1.2 Hz), 6.6 (1H, s), 3.98 (3H, s), 3.8 (3H, s), 3.72 (3H, s), 3.56 (2H, m), 2.97 (2H, m).

Sources & evidence

ORD record
ord-e607b9d797b647b9ae7305aae59b2b62
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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