(5,6-Dimethyl-1H-benzimidazol-1-yl)acetic acid → N-[1-[2-(4-chlorophenyl)oxazol-5-yl]-2-(3,5-difluorophenyl)ethyl]-2-(5,6-dimethylbenzimidazol-1-yl)acetamide

HRID 1506648Notes

Reaction equation

HRID 1506648 reaction equation
FC1C=C(C[C@H](NC(=O)CN2C3CCCCC=3C(C(F)(F)F)=N2)C2N(C3C=CC(OC)=CC=3)C=CN=2)C=C(F)C=1.Cl.[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:50][C:51]([CH:54]([NH2:64])[CH2:55][C:56]3[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=3)=[CH:52][N:53]=2)=[CH:45][CH:44]=1.[CH3:65][C:66]1[C:78]([CH3:79])=[CH:77][C:69]2[N:70]([CH2:73][C:74](O)=[O:75])[CH:71]=[N:72][C:68]=2[CH:67]=1>>[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:50][C:51]([CH:54]([NH:64][C:74](=[O:75])[CH2:73][N:70]3[C:69]4[CH:77]=[C:78]([CH3:79])[C:66]([CH3:65])=[CH:67][C:68]=4[N:72]=[CH:71]3)[CH2:55][C:56]3[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=3)=[CH:52][N:53]=2)=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 424323(5,6-Dimethyl-1H-benzimidazol-1-yl)acetic acidHCID 902803201-(2-(4-Chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethanamine hydrochlorideHCID 90281246N-[(1S)-2-(3,5-difluorophenyl)-1-[1-(4-methoxyphenyl)imidazol-2-yl]ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

Product 1

HCID 90290343N-[1-[2-(4-chlorophenyl)oxazol-5-yl]-2-(3,5-difluorophenyl)ethyl]-2-(5,6-dimethylbenzimidazol-1-yl)acetamide

Procedure

The title compound was prepared according to the method presented for the synthesis of compound 5F of Example 5 utilizing 19E and 2-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)acetic acid. 1H NMR (400 MHz, DMSO) δ 9.06-8.94 (m, 2H), 8.10 (s, 1H), 7.92 (d, J=8.5 Hz, 2H), 7.57 (d, J=8.6 Hz, 2H), 7.50 (s, 1H), 7.17 (s, 1H), 6.97 (m, 3H), 5.17-4.95 (m, 3H), 3.24-3.07 (m, 1H), 3.04 (dd, J=13.7, 9.7 Hz, 1H), 2.29 (s, 1H), 2.22 (s, 1H). MS (m/z) 520.9 [M+H]+.

Sources & evidence

ORD record
ord-c50de51802f24db6b3923dbbd316a36c
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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