1-Hydroxybenzotriazole → HCID 11696286, compound

HRID 646422Notes

Reaction equation

HRID 646422 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)#[N:2].[Li].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:49]1[CH2:53][CH2:52][CH2:51][C@H:50]1[CH2:54][N:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1>CN(C=O)C.ClCCl>[N:55]1([CH2:54][C@@H:50]2[CH2:51][CH2:52][CH2:53][N:49]2[C:12]([C:11]2[CH:10]=[CH:9][C:8]([C:7]3[CH:6]=[CH:5][S:4][C:3]=3[C:1]#[N:2])=[CH:16][CH:15]=2)=[O:14])[CH2:59][CH2:58][CH2:57][CH2:56]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 18946849HCID 18946849, compound

Product 1

HCID 11696286HCID 11696286, compoundYield 66%

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 5 mL 20% DMF/dichloromethane using 4-(2-cyano-thiophen-3-yl)-benzoic acid, lithium salt (141 mg, 0.60 mmol), EDC-HCl (143 mg, 0.75 mmol), HOBt (101 mg, 0.75 mmol), DIEA (0.24 mL, 1.4 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (77 mg, 0.50 mmol) to give the title compound (120 mg, 66% yield). MS (ES+) 366.3 (M+H)+

Sources & evidence

ORD record
ord-75d546c56c80434591ad6d01dbc44be5
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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