Hydrazine → HCID 178511483, compound

HRID 1888236Notes

Reaction equation

HRID 1888236 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.O=C1CCC(=O)[N:37]1[CH2:42][CH2:43][S:44](Cl)(=[O:46])=[O:45].NN>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH2:37][CH2:42][CH2:43][S:44]([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:46])=[O:45]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 185240132-(2,5-Dioxo-pyrrolidin-1-yl)-ethanesulfonyl chlorideHCID 1784795395-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride

Product 1

HCID 178511483HCID 178511483, compoundYield 17%

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 (25 mg, 0.014 mmol) and 2-(2,5-dioxo-1-pyrrolidinyl)ethanesulfonyl chloride (53 mg, 0.168 mmol). After the reaction mixture was stirred at room temperature overnight, hydrazine (4 eq) was 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 (10 mg, 17%)

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-7ec8e608db3b4f5792ff7387d5ac8456
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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