1-Hydroxybenzotriazole → HCID 11582478, compound

HRID 646420Notes

Reaction equation

HRID 646420 reaction equation
[CH3:1][S:2]([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].[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>[CH3:1][S:2]([C:5]1[S:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:51]3[CH2:55][CH2:54][CH2:53][C@H:52]3[CH2:56][N:57]3[CH2:61][CH2:60][CH2:59][CH2:58]3)=[O:16])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 59264695HCID 59264695, compound

Product 1

HCID 11582478HCID 11582478, compoundYield 57%

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 8 mL 37% DMF/dichloromethane using 4-(5-methanesulfonyl-thiophen-2-yl)-benzoic acid, Lithium salt (92 mg, 0.32 mmol), EDC-HCl (92 mg, 0.48 mmol), HOBt (65 mg, 0.48 mmol), DIEA (0.14 mL, 0.8 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (45 mg, 0.29 mmol) to give the title compound (60 mg, 57% yield). MS (ES+) 419.2 (M+H)+

Sources & evidence

ORD record
ord-09cb477e5aa040318ebc36697db49be3
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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