N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide → HCID 178484428, compound

HRID 2205647Notes

Reaction equation

HRID 2205647 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][N:6]=1)=[O:4].Br[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:45][CH2:44][CH2:43][C@@:30]3([C:34](=[O:35])[N:33]([C@H:36]4[CH2:41][CH2:40][C@@H:39]([OH:42])[CH2:38][CH2:37]4)[CH2:32][CH2:31]3)[CH2:29]2)=[C:24]([F:46])[CH:23]=1>>[F:46][C:24]1[CH:23]=[C:22]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([N:2]([CH3:1])[CH3:20])=[O:4])=[N:6][CH:7]=2)[CH:27]=[CH:26][C:25]=1[N:28]1[CH2:45][CH2:44][CH2:43][C@@:30]2([C:34](=[O:35])[N:33]([C@H:36]3[CH2:37][CH2:38][C@@H:39]([OH:42])[CH2:40][CH2:41]3)[CH2:32][CH2:31]2)[CH2:29]1

Participants

3

Reactant 2

HCID 57416491N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamideHCID 178517853HCID 178517853, compound

Product 1

HCID 178484428HCID 178484428, compound

Procedure

This compound was prepared by using procedures that were analogous to those described for the synthesis of Example 1, Step 8 starting from N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide and (5S)-7-(4-bromo-2-fluorophenyl)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one. LC/MS m/e 495.3 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): 8.86 (1H, d, J=1.7 Hz), 8.15 (1H, dd, J=8.1, 2.3 Hz), 7.51-7.65 (3H, m), 7.12 (1H, t, J=8.9 Hz), 4.37 (1H, d, J=3.1 Hz), 3.78 (1H, m), 3.71 (1H, m), 3.22-3.38 (3H, m), 3.06 (1H, d, J=11.7 Hz), 3.00 (3H, s), 2.97 (3H, s), 2.64-2.74 (2H, m), 2.18-2.27 (1H, m), 1.60-1.91 (8H, m), 1.39-1.51 (3H, m), 1.22-1.30 (2H, m).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a2896a0090704599ac1cb884a2bcac35
Source dataset
uspto-grants-2016_06
Patent number
US09371323B2

Reaction notes

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