4-(4-(Dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid → 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid

HRID 529031Notes

Reaction equation

HRID 529031 reaction equation
C(N(CCCC)C(C1N=C(C2C=CC(C(O)=O)=CC=2C(N2CCC3C(=CC=CC=3)C2)=O)N(C)C=1)=O)CCC.[CH2:39]([N:43]([CH2:74][CH2:75][CH2:76][CH3:77])[C:44]([C:46]1[N:47]=[CH:48][N:49]([CH3:73])[C:50]=1[C:51]1[CH:60]=[CH:59][C:54]([C:55]([O:57]C)=[O:56])=[CH:53][C:52]=1[C:61]([N:63]1[CH2:72][CH2:71][C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH2:64]1)=[O:62])=[O:45])[CH2:40][CH2:41][CH3:42]>>[CH2:39]([N:43]([CH2:74][CH2:75][CH2:76][CH3:77])[C:44]([C:46]1[N:47]=[CH:48][N:49]([CH3:73])[C:50]=1[C:51]1[CH:60]=[CH:59][C:54]([C:55]([OH:57])=[O:56])=[CH:53][C:52]=1[C:61]([N:63]1[CH2:72][CH2:71][C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH2:64]1)=[O:62])=[O:45])[CH2:40][CH2:41][CH3:42]

Participants

3

Reactant 2

HCID 710623034-(4-(Dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acidHCID 71062493Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Product 1

HCID 710622164-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acidYield 77.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 264L, methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (400 mg, 0.75 mmol) was converted to the title compound (300 mg, 77%). MS(ESI+) m/z 517.6 (M+H)+.

Sources & evidence

ORD record
ord-6d831d445d564b9d8908f19efbf1a9f8
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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