2-{5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl}acetic acid → N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide

HRID 1506646Notes

Reaction equation

HRID 1506646 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][O:66][C:67]1[N:72]=[C:71]2[C:73]([CH2:76][C:77](O)=[O:78])=[CH:74][NH:75][C:70]2=[CH:69][CH:68]=1>>[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:50][C:51]([CH:54]([NH:64][C:77](=[O:78])[CH2:76][C:73]3[C:71]4=[N:72][C:67]([O:66][CH3:65])=[CH:68][CH:69]=[C:70]4[NH:75][CH:74]=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 711869832-{5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-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 90281531N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide

Procedure

The title compound (6.0 mg) was prepared according to the method presented for the synthesis of compound 5F of Example 5 utilizing 19E and 2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetic acid. 1H NMR (400 MHz, DMSO) δ 11.6 (br, 1H), 8.50 (d, J=8.5 Hz, 1H), 8.40 (s, 1H), 8.01 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.55 (d, J=8.6 Hz, 3H), 7.03 (s, 1H), 6.83 (d, J=7.8 Hz, 3H), 5.08 (d, J=5.3 Hz, 1H), 3.82 (s, 3H), 3.44 (s, 2H), 3.23-3.06 (m, 1H), 3.04-2.91 (m, 1H). MS (m/z) 523.1 [M+H]+.

Sources & evidence

ORD record
ord-59ae48ad831b4aa6b28fba28dd5a5048
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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