Water → HCID 66581074, compound

HRID 1521865Notes

Reaction equation

HRID 1521865 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:27][S:26](=[O:29])(=[O:28])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:11]=3[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:40]([NH:47][CH2:48][CH2:49][CH2:50]Br)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].O>C1COCC1>[N:1]1([C:7]([C:9]2[C:10]3[CH:27]([CH2:50][CH2:49][CH2:48][NH:47][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[S:26](=[O:28])(=[O:29])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:11]=3[N:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 4460490tert-butyl N-(3-bromopropyl)carbamate2×HCID 66578983HCID 66578983, compound

Product 1

HCID 66581074HCID 66581074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (150 mg; 0.37 mmol; 1 eq.) in THF (3 mL) is added potassium bis(trimethylsilyl)amide (879.19 μl; 0.5 M; 0.44 mmol; 1.2 eq.) and then 3-(boc-amino)propyl bromide (104.68 mg; 0.44 mmol; 1.20 eq.) The reaction mixture is stirred at rt for 2 days. The reaction is not complete even after addition of 2 eq. of 3-(boc-amino)propyl bromide. It is stopped by addition of water. The product is extracted with EtOAc and the combined organic phases are washed with brine, dried over MgSO4 and concentrated under reduced pressure, to afford 217 mg (quant) of the title compound. HPLC (max plot) 83.1%; Rt 4.08 min. MS (ESI−): 565.5.

Workup

  1. extractionThe product is extracted with EtOAc
  2. washthe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37b53c4aab8942a1a70875e9ed68e93e
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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