1-Hydroxybenzotriazole → HCID 59264670, compound

HRID 646426Notes

Reaction equation

HRID 646426 reaction equation
[C:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:5]=1)(=[O:3])[NH2:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:49][C@@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[CH2:55][C@@H:56]1[CH2:60][CH2:59][CH2:58][NH:57]1>CN(C=O)C.C(Cl)Cl>[CH3:49][C@@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[CH2:55][C@@H:56]1[CH2:60][CH2:59][CH2:58][N:57]1[C:13]([C:12]1[CH:11]=[CH:10][C:9]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[S:8][CH:7]=2)=[CH:17][CH:16]=1)=[O:15]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidineHCID 59264652HCID 59264652, compound

Product 1

HCID 59264670HCID 59264670, compoundYield 14.4%

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 30% DMF/CH2Cl2 using 4-(5-Carbamoyl-thiophen-3-yl)-benzoic acid (360 mg, 1.6 mmol), EDC-HCl (439 mg, 2.3 mmol), HOBt (311 mg, 2.3 mmol), DIEA (0.70 mL, 4.0 mmol) and 2-(R)-Methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine (236 mg, 1.4 mmol) to give the title compound (80 mg, 14% yield). MS (ES+) 398.3 (M+H)+

Sources & evidence

ORD record
ord-c92ec8ee281b4ebf9458d1c4a9fdd227
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

Loading…