Sodium Iodide → HCID 68228591, compound

HRID 1521876Notes

Reaction equation

HRID 1521876 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].Cl[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:22]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[S:29](=[O:32])(=[O:31])[CH2:30][C:21]=3[C:20]([C:33]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[O:34])=[N:19]2)[CH2:13]1.[Na+].[I-]>C(#N)C.C(Cl)Cl>[N:35]1([C:33]([C:20]2[C:21]3[CH2:30][S:29](=[O:32])(=[O:31])[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:22]=3[N:18]([CH:14]3[CH2:15][CH2:16][CH2:17][N:12]([CH2:11][CH2:10][N:1]4[CH2:5][CH2:4][CH2:3][C:2]4=[O:6])[CH2:13]3)[N:19]=2)=[O:34])[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 66578955HCID 66578955, compound

Product 1

HCID 68228591HCID 68228591, compoundYield 9.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-pyrrolidone (35 mg; 0.42 mmol; 2 eq.) with NaH (10 mg; 0.42 mmol; 2 eq.) in ACN at 0° C. is added to a solution of enantiomer B of 1-[1-(2-chloroethyl)piperidin-3-yl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (100 mg; 0.21 mmol; 1 eq.) and NaI (31 mg; 0.21 mmol; 1 eq.) in ACN (2 mL). Reaction mixture is heated to 60° C. for 18 h after which DCM is added and organic phase is washed with water and brine. It is dried over MgSO4 then purified by MD-Autoprep to give 11 mg (9%) of the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.05 (d, J=7.7 Hz, 1H), 8.00-7.82 (m, 2H), 7.81-7.67 (m, 1H), 4.89-4.64 (m, 3H), 4.00-3.83 (m, 2H), 3.83-3.56 (m, 8H), 3.22-3.12 (m, 1H), 2.99-2.82 (m, 1H), 2.67-2.34 (m, 4H), 2.29-2.15 (m, 2H), 2.15-1.54 (m, 8H). MS (ESI+): 528.5. HPLC (max plot) 97.6%; Rt 1.86 min.

Workup

  1. customReaction mixture
  2. additionis added
  3. washorganic phase is washed with water and brine
  4. dry with materialIt is dried over MgSO4
  5. customthen purified by MD-Autoprep

Sources & evidence

ORD record
ord-9d1448df9c78498898aa2ccc7fe99beb
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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