Sodium Iodide → tert-butyl 3-((4-oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1751025Notes

Reaction equation

HRID 1751025 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:49](=[O:50])[CH2:48][O:47][C:46]2[CH:51]=[CH:52][CH:53]=[CH:54][C:45]1=2>CC(=O)CC>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:41][CH2:42][CH2:43][N:44]3[C:49](=[O:50])[CH2:48][O:47][C:46]4[CH:51]=[CH:52][CH:53]=[CH:54][C:45]3=4)[CH2:8][CH2:7]2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=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])([CH3:26])[CH3:27])=[O:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-oneHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046693tert-butyl 3-((4-oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 35%

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 4-(3-chloropropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.107 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 (0.1 g, 35%); 1H NMR (DMSO-d6): δ 1.52 (s, 9H), 1.62 (d, 2H, J=12.8 Hz), 1.75 (t, 2H, J=6.8 Hz), 2.40 (t, 2H, J=7.2 Hz), 2.45-2.62 (m, 2H), 2.66-2.73 (m, 4H), 3.99 (t, 2H, J=7.2 Hz), 4.58-4.63 (m, 6H), 6.76 (t, 1H, J=7.2 Hz), 6.85 (d, 2H, J=8.4 Hz), 7.00 (m, 3H), 7.21 (t, 2H, J=7.2 Hz), 7.33-7.34 (m, 1H), 7.48-7.55 (m, 2H), 7.79 (s, 1H), 7.83 (d, 1H, J=7.2 Hz); MS for C36H42N4O5 m/z 611.12 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-31586a5316bc40e8ab509622704b3c63
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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