3-Pyridinecarbonyl chloride, hydrochloride (1:1) → Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]pyridin-3-ylmethylamine

HRID 1950071Notes

Reaction equation

HRID 1950071 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C(=CC=C(OC)C=2)C1)C.Cl.C(Cl)(=O)C1C=CC=NC=1.[CH2:34]([N:36]([C:45]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:46]=1[CH:53]1[CH2:62][CH2:61][C:60]2[C:55](=[CH:56][CH:57]=[C:58]([O:63][CH3:64])[CH:59]=2)[CH2:54]1)[C:37]([C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)=O)[CH3:35]>>[CH2:34]([N:36]([C:45]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:46]=1[CH:53]1[CH2:62][CH2:61][C:60]2[C:55](=[CH:56][CH:57]=[C:58]([O:63][CH3:64])[CH:59]=2)[CH2:54]1)[CH2:37][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)[CH3:35]

Participants

4

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 23087318Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineHCID 66626143Pyridine-3-carboxylic acid ethyl [5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide

Product 1

HCID 66627111Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]pyridin-3-ylmethylamineYield 19.2%

Procedure

Synthesized from ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine and nicotinoyl chloride hydrochloride according to an analogous synthetic method to Preparation Example 86, pyridine-3-carboxylic acid ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide (162 mg) was used according to an analogous synthetic method to Example 337 described below to provide ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]pyridin-3-ylmethylamine (30 mg). The total amount of this compound was used according to an analogous synthetic method to Example 111 described below to provide the title compound (23 mg).

Sources & evidence

ORD record
ord-0dc10fd98bfa4a4dbd442d136d9cb6fb
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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