(3S)-Piperidin-3-ol--hydrogen chloride (1/1) → HCID 89908069, compound

HRID 923957Notes

Reaction equation

HRID 923957 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 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)HCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89908069HCID 89908069, 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 (S)-3-hydroxypiperidine hydrochloride to afford a brown oil. UPLC-MS (condition 1) tR=3.36 min, m/z=460.0-462.0, m/z=458.0-460.1; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.28-1.41 (m, 1H) 1.49-1.63 (m, 1H) 1.75-1.84 (m, 1H) 1.90-1.97 (m, 1H) 2.73 (dd, J=12.10, 9.17 Hz, 1H) 2.87-2.96 (m, 1H) 3.59-3.68 (m, 1H) 3.75 (d, J=12.72 Hz, 1H) 3.87-3.95 (m, 1H) 4.88 (s, 1H) 7.36 (d, J=8.80 Hz, 2H) 7.82-7.88 (m, 2H) 8.42 (d, J=1.96 Hz, 1H) 8.76 (d, J=1.96 Hz, 1H) 10.37 (s, 1H).

Workup

  1. customto afford a brown oil

Sources & evidence

ORD record
ord-9db94c155c334e2b85f1c95689dde13d
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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