Sodium Iodide → HCID 178513528, compound

HRID 1888283Notes

Reaction equation

HRID 1888283 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.[I-].[Na+]>C(#N)C>[N:38]1([CH2:2][CH2:3][CH2:4][S:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:21]=4)[NH:16][N:15]=3)[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 178513524HCID 178513524, compound2×

Product 1

HCID 178513528HCID 178513528, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indazole-7-carboxamide (Intermediate 22) (20 mg, 0.0435 mmol) in acetonitrile (1 mL) was added K2CO3 (27 mg, 0.174 mmol), morpholine (19 uL, 0.219 mmol) and sodium iodide (0.8 mg, 0.00435 mmol). The reaction mixture was heated to 60° C. for 14 hrs. The solution was filtered and concentrated. The residue was purified by using a Gilson semi-preparative HPLC system with a YMC ODS-A (C-18) column 50 mm by 20 mm ID, eluting with 10% B to 80% B in 10 min, hold for 1 min where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (3.6 mg, 16%).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customThe residue was purified
  4. washeluting with 10% B to 80% B in 10 min

Sources & evidence

ORD record
ord-ece2ad185e514a0eb038dec9dbfb9ab4
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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