Hydrochloric Acid → 1-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1892616Notes

Reaction equation

HRID 1892616 reaction equation
C(OC(N1CCC2C(=CC(OC)=C(OC)C=2)C1CC1C=CC(Br)=CC=1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].[C:55]([O:59][C:60]([N:62]1[CH2:71][CH2:70][C:69]2[C:64](=[CH:65][C:66]([O:74][CH3:75])=[C:67]([O:72][CH3:73])[CH:68]=2)[CH:63]1[CH2:76][C:77]1[CH:82]=[CH:81][C:80]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][C:84]=2[NH:89][C:90](=[O:92])[CH3:91])=[CH:79][CH:78]=1)=[O:61])([CH3:58])([CH3:57])[CH3:56].[ClH:93]>C(O)(C)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:55]([O:59][C:60]([N:62]1[CH2:71][CH2:70][C:69]2[C:64](=[CH:65][C:66]([O:74][CH3:75])=[C:67]([O:72][CH3:73])[CH:68]=2)[CH:63]1[CH2:76][C:77]1[CH:78]=[CH:79][C:80]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][C:84]=2[NH:89][C:90](=[O:92])[CH3:91])=[CH:81][CH:82]=1)=[O:61])([CH3:58])([CH3:56])[CH3:57].[ClH:93].[CH3:73][O:72][C:67]1[CH:68]=[C:69]2[C:64](=[CH:65][C:66]=1[O:74][CH3:75])[CH:63]([CH2:76][C:77]1[CH:78]=[CH:79][C:80]([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][C:84]=3[NH:89][C:90](=[O:92])[CH3:91])=[CH:81][CH:82]=1)[NH:62][CH2:71][CH2:70]2

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 589064711-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 597442891-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 2

HCID 597442891-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 69270574N-[4'-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-biphenyl-2-yl]acetamide hydrochloride salt

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

1-(2′-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 17 was synthesized by the Suzuki coupling of 1-(4-bromobenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 1 with 2-acethylaminophenylboronic acid 16 using Palladium(II) acetate, triphenylphosphine, and Na2CO3 in anhydrous isopropanol. Reaction of compound 17 with 2 M HCl solution in diethylether yielded N-[4′-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-biphenyl-2-yl]acetamide hydrochloride salt 18 (Scheme-5).

Sources & evidence

ORD record
ord-7a3fb91fe2b74c82acd27e4e6cc16a0e
Source dataset
uspto-grants-2013_08
Patent number
US08507523B2

Reaction notes

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