1-Hydroxybenzotriazole → HCID 11494333, compound

HRID 646413Notes

Reaction equation

HRID 646413 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:48]1[CH2:52][CH2:51][CH2:50][C@H:49]1[CH2:53][N:54]1[CH2:58][CH2:57][CH2:56][CH2:55]1>CN(C=O)C.ClCCl>[N:54]1([CH2:53][C@@H:49]2[CH2:50][CH2:51][CH2:52][N:48]2[C:12]([C:11]2[CH:10]=[CH:9][C:8]([C:6]3[S:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[CH:16][CH:15]=2)=[O:14])[CH2:58][CH2:57][CH2:56][CH2:55]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 155439354-(5-Cyanothiophen-2-yl)benzoic acid

Product 1

HCID 11494333HCID 11494333, compoundYield 64%

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 100 mL 10% DMF/dichloromethane using 4-(5-cyano-thiophen-2-yl)-benzoic acid (CAS 402765-55-9) (2.75 g, 12.0 mmol), EDC-HCl (3.44 g, 18.0 mmol), HOBt (2.43 g, 18.0 mmol), DIEA (5.22 mL, 30 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.54 g, 10.0 mmol) to give the title compound (2.33 g, 64% yield). MS (ES+) 366.2 (M+H)+

Sources & evidence

ORD record
ord-9e9ecfd61e9f4824aaa17b9cc6dac8bf
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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