Sodium Iodide → HCID 178513529, compound

HRID 1888282Notes

Reaction equation

HRID 1888282 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+].[CH:38]1([NH2:42])[CH2:41][CH2:40][CH2:39]1.[I-].[Na+]>CN(C=O)C>[CH:38]1([NH:42][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])[CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 178513524HCID 178513524, compound2×

Product 1

HCID 178513529HCID 178513529, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °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 DMF (1 mL) was added K2CO3 (27 mg, 0.174 mmol), cyclobutyl amine (18 uL, 0.217 mmol) and sodium iodide (0.8 mg, 0.00438 mmol). The reaction mixture was heated to 120° 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 (4.1 mg, 19%).

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-458d533847ba467daa25bcf6bbc9bcbd
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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