Sodium Iodide → HCID 178513525, compound

HRID 1888281Notes

Reaction equation

HRID 1888281 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[CH2:42][CH2:41][CH2:40][CH2:39]1.[I-].[Na+]>C(#N)C>[C:23]1([C:20]2[CH:21]=[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=2)[NH:16][N:15]=[C:14]3[CH:11]2[CH2:12][CH2:13][N:8]([S:5]([CH2:4][CH2:3][CH2:2][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)(=[O:7])=[O:6])[CH2:9][CH2:10]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 178513524HCID 178513524, compound2×

Product 1

HCID 178513525HCID 178513525, compoundYield 28.5%

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) (18 mg, 0.039 mmol) in acetonitrile (2 mL) was added K2CO3 (25 mg, 0.156 mmol), pyrrolidine (19 uL, 0.196 mmol) and sodium iodide (0.7 mg, 0.0039 mmol). The reaction mixture was heated to 60° C. overnight. 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 (5.5 mg, 28%).

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-544d666620c74680b7eb03fc5fdb538c
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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