Sodium Iodide → N-(3-((4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide

HRID 1751139Notes

Reaction equation

HRID 1751139 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]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][CH2:40][CH2:41][N:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2([CH2:52][CH2:51]2)[C:43]1=[O:53]>CC(=O)CC>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:39][CH2:40][CH2:41][N:42]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:44]4([CH2:52][CH2:51]4)[C:43]3=[O:53])[CH2:10][CH2:11]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]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 580467761'-(3-Chloropropyl)spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 66652299N-(3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide

Product 1

HCID 66652169N-(3-((4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamideYield 31%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of N-(3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide (0.2 g, 0.48 mmol), sodium iodide (0.029 g, 0.19 mmol) and potassium carbonate (0.133 g, 0.96 mmol) in 2-butanone (5 mL), was added 1′-(3-chloropropyl)spiro[cyclopropane-1,3′-indolin]-2′-one (0.114 g, 0.48 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.09 g, 31%); 1H NMR (DMSO-d6): δ 1.51 (t, 2H, J=3.6 Hz), 1.58 (t, 2H, J=3.6 Hz), 1.64 (d, 2H, J=13.2 Hz), 1.80 (br, 2H), 2.37 (br, 2H), 2.51-2.57 (m, 2H), 2.68-2.73 (m, 4H), 2.96 (s, 3H), 3.82 (t, 2H, J=6.8 Hz), 4.52 (s, 2H), 4.58 (s, 2H), 6.76 (t, 1H, J=7.6 Hz), 6.84 (d, 2H, J=8.4 Hz), 6.96-7.02 (m, 3H), 7.09 (s, 1H), 7.12 (d, 1H, J=8 Hz), 7.17-7.24 (m, 4H), 7.32 (t, 1H, J=8 Hz), 9.81 (s, 1H); MS for C34H39N5O4S m/z 614.4 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-85160dbf3f944bc1a85589de088da341
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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