Sodium Iodide → HCID 66580618, compound

HRID 1521860Notes

Reaction equation

HRID 1521860 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([N:10]2[C:14]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[S:21](=[O:24])(=[O:23])[CH2:22][C:13]=3[C:12]([C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])=[N:11]2)[CH2:5]1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)Cl>[N:27]1([C:25]([C:12]2[C:13]3[CH2:22][S:21](=[O:23])(=[O:24])[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:14]=3[N:10]([CH:6]3[CH2:7][CH2:8][CH2:9][N:4]([CH2:3][CH2:2][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:5]3)[N:11]=2)=[O:26])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 66578955HCID 66578955, compound

Product 1

HCID 66580618HCID 66580618, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Enantiomer A of 1- [1-(2-chloroethyl)piperidin-3-yl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (274 mg; 0.57 mmol; 1.00 eq.), morpholine (199 μl; 2.29 mmol; 4.00 eq.), sodium iodide (85 mg; 0.57 mmol; 1.00 eq.) and K2CO3 (237 mg; 1.72 mmol; 3.00 eq.) are taken up in ACN (6 mL). The reaction mixture is stirred at 60° C. overnight. The reaction mixture is diluted in DCM and washed with water, brine, then dried over MgSO4 and evaporated. Purification by flash chromatography (DCM/MeOH 0 to 5%) followed by dissolution in ACN : water and freeze drying gives the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.05 (dd, J =1.2, 7.8 Hz, 1H), 7.94 (td, J =1.3, 7.8 Hz, 1H), 7.88-7.81 (m, 11-1), 7.80-7.70 (m, 1H), 5.05-4.62 (m, 3H), 4.05-3.79 (m, 2H), 3.79-3.58 (m, 6H), 3.56-3.42 (m, 4H), 3.32-3.08 (m, 3I-1), 2.91 (d, J =10.8 Hz, 1H), 2.46-2.22 (m, 8H), 2.20-1.60 (m, 6H). MS (ESI+): 530.46. HPLC (max plot) 99.4%; Rt 1.56 min. [α]25D+4.20 (c 1.09, DCM).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography (DCM/MeOH 0 to 5%)
  5. dissolutionfollowed by dissolution in ACN
  6. dry with materialwater and freeze drying

Sources & evidence

ORD record
ord-b81e6d4a0e444e729d2d607fef192f84
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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