Diisopropylethylamine → HCID 178433558, compound

HRID 1888235Notes

Reaction equation

HRID 1888235 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.C(N(C(C)C)CC)(C)C.[CH3:35][N:36]1[CH:40]=[C:39]([S:41](Cl)(=[O:43])=[O:42])[N:38]=[C:37]1[CH3:45]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:35][N:36]1[CH:40]=[C:39]([S:41]([N:23]2[CH2:24][CH2:25][CH:20]([C:11]3[C:10]4[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH:9]=4)[NH:13][N:12]=3)[CH2:21][CH2:22]2)(=[O:43])=[O:42])[N:38]=[C:37]1[CH3:45]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27362561,2-Dimethylimidazole-4-sulfonyl chlorideHCID 1784795395-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride

Product 1

HCID 178433558HCID 178433558, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

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 (20 mg, 0.014 mmol) and 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride (33 mg, 0.168 mmol). The reaction mixture was stirred at room temperature overnight. 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 (25 mg, 37%)

Workup

  1. filtrationThe solution was filtered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified
  4. 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-d9533e9a53a0445e829db49a717b9fb7
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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