1-Hydroxybenzotriazole → HCID 11639623, compound

HRID 646419Notes

Reaction equation

HRID 646419 reaction equation
[CH3:1][S:2][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.[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>[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:49]3[CH2:53][CH2:52][CH2:51][C@H:50]3[CH2:54][N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:14])=[CH:15][CH:16]=2)=[CH:5][CH:4]=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 59264689HCID 59264689, compound

Product 1

HCID 11639623HCID 11639623, compoundYield 71%

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-methylsulfanyl-thiophen-2-yl)-benzoic acid, Lithium salt (51 mg, 0.20 mmol), EDC-HCl (57 mg, 0.30 mmol), HOBt (41 mg, 0.30 mmol), DIEA (0.09 mL, 0.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (28 mg, 0.18 mmol) to give the title compound (50 mg, 71% yield). MS (ES+) 387.7 (M+H)+

Sources & evidence

ORD record
ord-32e12f58c23c4a40999816e76c0cb1b9
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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