Cyclopentylamine → HCID 178513530, compound

HRID 1888286Notes

Reaction equation

HRID 1888286 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([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39]1.[I-].[Na+]>CN(C=O)C>[CH:38]1([NH:43][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])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178513524HCID 178513524, compound2×

Product 1

HCID 178513530HCID 178513530, compoundYield 26.1%

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) (19 mg, 0.0413 mmol) in DMF (1 mL) was added K2CO3 (25 mg, 0.165 mmol), cyclopentylamine (22 uL, 0.2065 mmol) and sodium iodide (1.0 mg). 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 (5.5 mg, 26%).

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-bc34ebfcfab64e7f94b1f0b197ef1a19
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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