1-Hydroxybenzotriazole → HCID 11675935, compound

HRID 646416Notes

Reaction equation

HRID 646416 reaction equation
[C:1]([C:6]1[S:10][C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Li].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[CH2:57][N:58]1[CH2:62][CH2:61][CH2:60][CH2:59]1>CN(C=O)C.ClCCl>[CH3:4][CH:2]([CH3:3])[C:1]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:52]3[CH2:56][CH2:55][CH2:54][C@H:53]3[CH2:57][N:58]3[CH2:62][CH2:61][CH2:60][CH2:59]3)=[O:17])=[CH:18][CH:19]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 59264661HCID 59264661, compound

Product 1

HCID 11675935HCID 11675935, 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 10 mL 50% DMF/dichloromethane using 4-(5-isobutyryl-thiophen-2-yl)-benzoic acid, lithium salt (96 mg, 0.34 mmol), EDC-HCl (97 mg, 0.51 mmol), HOBt (69 mg, 0.51 mmol), DIEA (0.09 mL, 0.51 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (48 mg, 0.31 mmol) to give the title compound (90 mg, 71% yield). MS (ES+) 411.2 (M+H)+

Sources & evidence

ORD record
ord-2838ca7394a0495b9d0b90c9ac25414e
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

Loading…