Sodium Iodide → HCID 58046660, compound

HRID 1751036Notes

Reaction equation

HRID 1751036 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][N:44]1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=[N:45]1>CC(=O)CC>[N:44]1([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)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=[N:45]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 52439381-(3-chloropropyl)-1H-1,2,3-benzotriazoleHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046660HCID 58046660, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

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 1-(3-chloropropyl)-1H-benzo[d][1,2,3]triazole (0.093 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 (0.21 g, 77%); 1H NMR (DMSO-d6): δ 1.51 (s, 9H), 1.58 (d, 2H, J=13.2 Hz), 2.13 (t, 2H, J=6.4 Hz), 2.30 (t, 2H, J=6.4 Hz), 2.49-2.53 (m, 2H), 2.66 (d, 4H, J=7.6 Hz), 4.58 (d, 4H, J=9.6 Hz), 4.80 (t, 2H, J=6.4 Hz), 6.78 (t, 1H, J=6.8 Hz), 6.84 (d, 2H, J=8 Hz), 7.25 (t, 2H, J=8 Hz), 7.39 (t, 1H, J=7.2 Hz), 7.47-7.54 (m, 3H), 7.78 (s, 1H), 7.82 (dt, 1H, J=6.8 and 2 Hz), 7.93 (d, 1H, J=8.4 Hz), 8.03 (d, 1H, J=8.4 Hz); MS for C34H40N6O3 m/z 581.20 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-cc27029405034ebd903ea6b533099da5
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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