1-Hydroxybenzotriazole → HCID 11625644, compound

HRID 646418Notes

Reaction equation

HRID 646418 reaction equation
[O:1]1[C:5]([C:6]2[S:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:51]1[CH2:55][CH2:54][CH2:53][C@H:52]1[CH2:56][N:57]1[CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C.ClCCl>[O:1]1[C:5]([C:6]2[S:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([N:51]4[CH2:55][CH2:54][CH2:53][C@H:52]4[CH2:56][N:57]4[CH2:61][CH2:60][CH2:59][CH2:58]4)=[O:17])=[CH:18][CH:19]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59264700HCID 59264700, compound

Product 1

HCID 11625644HCID 11625644, compoundYield 48%

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 9 mL 50% DMF/dichloromethane using 4-(5-oxazol-5-yl-thiophen-2-yl)-benzoic acid (133 mg, 0.49 mmol), EDC-HCl (143 mg, 0.75 mmol), HOBt (101 mg, 0.75 mmol), DIEA (0.22 mL, 1.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (63 mg, 0.41 mmol) to give the title compound (80 mg, 48% yield). MS (ES+) 408.3 (M+H)+

Sources & evidence

ORD record
ord-d515a0a0acc54477b847ad3820575919
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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