2-Oxa-6-azaspiro[3.4]octane → HCID 118195257, compound

HRID 923944Notes

Reaction equation

HRID 923944 reaction equation
[Br:1][C:2]1[C:3](N2CC[C@@H](O)C2)=[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].[CH2:28]1[C:31]2([CH2:35][CH2:34][NH:33][CH2:32]2)[CH2:30][O:29]1>>[Br:1][C:2]1[C:3]([N:33]2[CH2:34][CH2:35][C:31]3([CH2:30][O:29][CH2:28]3)[CH2:32]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:19])([F:18])[F:20])=[CH:14][CH:15]=1)=[O:8]

Participants

3

Reactant 2

HCID 534383232-Oxa-6-azaspiro[3.4]octaneHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195257HCID 118195257, 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 2-oxa-6-azaspiro[3,4]octane to afford white needles. UPLC-MS (condition 1) tR=2.93 min, m/z=471.9/473.9 [M+H]+, m/z=469.9/471.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.20 (t, J=6.85 Hz, 2H) 3.73 (t, J=6.97 Hz, 2H) 3.95 (s, 2H) 4.51 (d, J=5.87 Hz, 2H) 4.60 (d, J=5.87 Hz, 2H) 7.35 (d, J=8.31 Hz, 2H) 7.82-7.88 (m, 2H) 8.36 (d, J=2.20 Hz, 1H) 8.69 (d, J=1.96 Hz, 1H) 10.24 (s, 1H).

Workup

  1. customto afford white needles

Sources & evidence

ORD record
ord-65970a8d938a44c288eeac09a5a0e5b9
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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