1-Hydroxybenzotriazole → HCID 11626297, compound

HRID 646421Notes

Reaction equation

HRID 646421 reaction equation
[N:1]1([C:6]([C:8]2[S:12][C:11]([C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:53]1[CH2:57][CH2:56][CH2:55][C@H:54]1[CH2:58][N:59]1[CH2:63][CH2:62][CH2:61][CH2:60]1>CN(C=O)C.ClCCl>[N:1]1([C:6]([C:8]2[S:12][C:11]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([N:53]4[CH2:57][CH2:56][CH2:55][C@H:54]4[CH2:58][N:59]4[CH2:63][CH2:62][CH2:61][CH2:60]4)=[O:18])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59264680HCID 59264680, compound

Product 1

HCID 11626297HCID 11626297, compoundYield 57.1%

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-[5-(Pyrrolidine-1-carbonyl)-thiophen-2-yl]-benzoic acid (121 mg, 0.40 mmol), EDC-HCl (115 mg, 0.60 mmol), HOBt (81 mg, 0.60 mmol), DIEA (0.17 mL, 1.0 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (52 mg, 0.34 mmol) to give the title compound (85 mg, 57% yield). MS (ES+) 438.3 (M+H)+

Sources & evidence

ORD record
ord-08aad30a7a6e43708db3b7d5ff8d1d78
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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