HCID 69826798, compound → HCID 89907977, compound

HRID 923895Notes

Reaction equation

HRID 923895 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].Cl.[CH3:24][O:25][C@@H:26]1[CH2:30][NH:29][CH2:28][C@H:27]1[OH:31]>>[Br:1][C:2]1[C:3]([N:29]2[CH2:30][C@@H:26]([O:25][CH3:24])[C@H:27]([OH:31])[CH2:28]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 69826798HCID 69826798, compoundHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89907977HCID 89907977, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 12.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2) and Trans-4-methoxy-3-pyrrolidinol hydrochloride to afford a white amorphous solid. UPLC-MS (condition 1) tR=2.65 min, m/z=475.9-477.9 [M+H]+, m/z=474.0-475.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.31 (s, 3H) 3.58 (d, J=11.49 Hz, 1H) 3.66 (d, J=12.23 Hz, 1H) 3.72-3.77 (m, 1H) 3.92 (dd, J=11.86, 4.28 Hz, 1H) 3.97 (dd, J=12.10, 4.28 Hz, 1H) 4.22 (br. s, 1H) 5.30 (d, J=3.18 Hz, 1H) 7.36 (d, J=8.31 Hz, 2H) 7.85 (d, J=9.29 Hz, 2H) 8.36 (d, J=2.20 Hz, 1H) 8.68 (d, J=2.20 Hz, 1H) 10.25 (s, 1H).

Workup

  1. customto afford a white amorphous solid

Sources & evidence

ORD record
ord-9a450b9a35c447eda726cc22fcc7edcc
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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