Sodium Iodide → HCID 178450674, compound

HRID 1751051Notes

Reaction equation

[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:41][CH2:42][CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][N:45]=1>CC(=O)CC>[NH:46]1[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:44]([CH2:43][CH2:42][CH2:41][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)=[N:45]1

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.2 g, 0.47 mmol), potassium carbonate (0.097 g, 0.7 mmol) and sodium iodide (0.021 g, 0.14 mmol) in 2-butanone (5 mL), was added 3-(3-chloropropyl)-1H-indazole (0.092 g, 0.47 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered, concentrated and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.06 g, 22%); 1H NMR (DMSO-d6): δ 1.52 (s, 9H), 1.64 (d, 2H, J=14 Hz), 1.95 (t, 2H, J=6.4 Hz), 2.59-2.85 (m, 8H), 2.96 (t, 2H, J=7.6 Hz), 4.60 (d, 4H, J=9.6 Hz), 6.76 (t, 1H, J=7.2 Hz), 6.85 (d, 2H, J=8 Hz), 7.06 (t, 1H, J=6.8 Hz), 7.21 (t, 2H, J=7.6 Hz), 7.31 (t, 1H, J=7.2 Hz), 7.44-7.53 (m, 3H), 7.74-7.84 (m, 3H), 12.63 (s, 1H); MS for C35H41N5O3 m/z 580.13 (M+H)+.

Workup

filtrationthe reaction mixture was filtered
concentrationconcentrated
customisolated by preparatory TLC (10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-a68ae8954de940bfa6c6c72f5ca4de19
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156840B2

Reaction notes

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