Dimethylamine → HCID 178483612, compound

HRID 1888239Notes

Reaction equation

HRID 1888239 reaction equation
Cl.[C:2]1([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][N:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([N:29]([CH:32]([CH3:34])C)[CH2:30]C)(C)C.ClCC[CH2:38][S:39](Cl)(=[O:41])=[O:40].[I-].[Na+].C([O-])([O-])=O.[K+].[K+].CNC>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:30][N:29]([CH3:26])[CH2:32][CH2:34][CH2:38][S:39]([N:23]1[CH2:24][CH2:25][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[NH:13][N:12]=2)[CH2:21][CH2:22]1)(=[O:41])=[O:40]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 154103-Chloropropanesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 1784795395-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride

Product 1

HCID 178483612HCID 178483612, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride (Example 2) (50 mg, 0.14 mmol) in DMF (3 mL) was added diisopropylethylamine (100 uL, 0.56 mmol), DMAP (25 mg, 0.014 mmol) and 3-chloro-1-propanesulfonyl chloride (28 uL, 0.21 mmol). After the reaction mixture was stirred at room temperature for 2 hrs, sodium iodide (20 mg), K2CO3 (40 mg) and 2M dimethyl amine in DMF (0.32 mL) were added. The reaction mixture was stirred for 4 hrs. The solution was filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (30 mg, 46%)

Workup

  1. stirringThe reaction mixture was stirred for 4 hrs
  2. filtrationThe solution was filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified
  5. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d22c44197a4a4292a5e57f3ee955692d
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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