Benzoyl chloride → HCID 178513521, compound

HRID 1888228Notes

Reaction equation

HRID 1888228 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(CC)CC)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[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][N:23]([C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:40])[CH2:22][CH2:21]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 1784795395-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride

Product 1

HCID 178513521HCID 178513521, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride (0.051 g, 0.17 mmols), triethylamine (0.1 mL, 0.71 mmols), DMAP (0.0021 g, 0.017 mmols), and benzoylchloride (0.020 mL, 0.17 mmols) in DMF (3 mL) was kept at ambient temperature overnight. The mixture was concentrated in vacuo and the resulting residue purified via preparative HPLC, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give 0.036 g of a white solid. LC/MS-M+H 425

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting residue purified via preparative HPLC
  3. 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-090432bc4b4546d0bf5ef3ac4832b5e1
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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