(3R)-piperidin-3-ol hydrochloride → HCID 89907836, compound

HRID 923953Notes

Reaction equation

HRID 923953 reaction equation
[Br:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]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].Cl.O[C@@H:30]1CCCNC1>>[Br:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:30][CH2:25][C@@H:24]([OH:27])[CH2:23]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:18])[F:19])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89907836HCID 89907836, 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 (Example 35) and (R)-(+)-3-hydroxypiperidine hydrochloride to afford a brown oil. UPLC-MS (condition 1) tR=3.38 min, m/z=460.0-462.0 [M+H]+, m/z=458.0-461.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.28-1.41 (m, 1H) 1.49-1.63 (m, 1H) 1.75-1.85 (m, 1H) 1.90-1.98 (m, 1H) 2.73 (dd, J=12.23, 9.29 Hz, 1H) 2.87-2.96 (m, 1H) 3.56-3.69 (m, 1H) 3.75 (d, J=12.72 Hz, 1H) 3.91 (dd, J=12.10, 3.55 Hz, 1H) 4.88 (s, 1H) 7.36 (d, J=8.80 Hz, 2H) 7.82-7.89 (m, 2H) 8.42 (d, J=2.20 Hz, 1H) 8.76 (d, J=2.20 Hz, 1H) 10.37 (s, 1H).

Workup

  1. customto afford a brown oil

Sources & evidence

ORD record
ord-9276c31c8f134c0fad89a05b234bde87
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…