1-Hydroxybenzotriazole → HCID 11517346, compound

HRID 646417Notes

Reaction equation

HRID 646417 reaction equation
[S:1]([C:5]1[S:9][C:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[Li].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:51]1[CH2:55][CH2:54][CH2:53][C@H:52]1[CH2:56][N:57]1[CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C.ClCCl>[N:57]1([CH2:56][C@@H:52]2[CH2:53][CH2:54][CH2:55][N:51]2[C:14]([C:13]2[CH:12]=[CH:11][C:10]([C:8]3[S:9][C:5]([S:1]([NH2:2])(=[O:3])=[O:4])=[CH:6][CH:7]=3)=[CH:18][CH:17]=2)=[O:16])[CH2:61][CH2:60][CH2:59][CH2:58]1

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 534263114-(5-Sulfamoylthiophen-2-yl)benzoic acid

Product 1

HCID 11517346HCID 11517346, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure D in 9 mL 50% DMF/dichloromethane using 4-(5-Sulfamoyl-thiophen-2-yl)-benzoic acid, lithium salt (173 mg, 0.61 mmol), EDC-HCl (174 mg, 0.91 mmol), HOBt (123 mg, 0.91 mmol), DIEA (0.26 mL, 1.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (79 mg, 0.51 mmol) to give the title compound (74 mg, 34% yield). MS (ES+) 420.2 (M+H)+

Sources & evidence

ORD record
ord-58483fd553a445e7934b9bdb9147c64e
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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