Chlorosuccinimide → HCID 71227677, compound

HRID 715521Notes

Reaction equation

HRID 715521 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[C:8]([N:10]2[CH2:14][C@@:13]3([CH2:19][CH2:18][CH2:17][C@@:16]([CH2:21][N:22]4[C:26]5[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=5[N:24]=[CH:23]4)([CH3:20])[CH2:15]3)[O:12][C:11]2=[O:33])[O:7][N:6]=1)([CH3:4])[CH3:3].C1C(=O)N([Cl:41])C(=O)C1>C(Cl)(Cl)Cl>[Cl:41][C:9]1[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[N:6][O:7][C:8]=1[N:10]1[CH2:14][C@@:13]2([CH2:19][CH2:18][CH2:17][C@@:16]([CH2:21][N:22]3[C:26]4[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=4[N:24]=[CH:23]3)([CH3:20])[CH2:15]2)[O:12][C:11]1=[O:33]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 71227656HCID 71227656, compound

Product 1

HCID 71227677HCID 71227677, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a vial was added 1-({(5S,7S)-3-[3-(1,1-dimethylethyl)-5-isoxazolyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitrile (85 mg, 0.190 mmol) and chloroform (950 μL) at RT, followed by NCS (25.4 mg, 0.190 mmol). The reaction mixture was stirred at RT followed by 65° C. for 5 h. Ater 22 h reaction at 65° C. the crude mixture was purified by reverse phase HPLC (30-80% MeCN/H2O, 0.1% TFA modifier, 30×150 mm Sunfire 18 column), and TFA salt of 1-({(5S,7S)-3-[4-chloro-3-(1,1-dimethylethyl)-5-isoxazolyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitrile was obtained (62.4 mg, 54% yield). MS (m/z) 482.2 (M+H+).

Workup

  1. customwas purified by reverse phase HPLC (30-80% MeCN/H2O, 0.1% TFA modifier, 30×150 mm Sunfire 18 column), and TFA salt of 1-({(5S,7S)-3-[4-chloro-3-(1,1-dimethylethyl)-5-isoxazolyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitrile
  2. customwas obtained (62.4 mg, 54% yield)

Sources & evidence

ORD record
ord-4eb45232404a4292a74a3936cea8dcc7
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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