1-Hydroxybenzotriazole → HCID 11582055, compound

HRID 646425Notes

Reaction equation

HRID 646425 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([F:17])[CH:9]=2)=[CH:5][CH:4]=1)#[N: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>[F:17][C:10]1[CH:9]=[C:8]([C:6]2[S:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:16]=[CH:15][C:11]=1[C:12]([N:57]1[CH2:58][CH2:59][CH2:60][C@H:56]1[CH2:55][N:51]1[CH2:52][CH2:53][CH2:54][C@H:50]1[CH3:49])=[O:14]

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 59264698HCID 59264698, compound

Product 1

HCID 11582055HCID 11582055, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure D in 6 mL DMF using 4-(5-cyano-thiophen-2-yl)-2-fluoro-benzoic acid (181 mg, 0.73 mmol), EDC-HCl (210 mg, 1.1 mmol), HOBt (149 mg, 1.1 mmol), DIEA (0.31 mL, 1.8 mmol) and 2-(R)-Methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine (101 mg, 0.60 mmol) to give the title compound (30 mg, 12% yield). MS (ES+) 398.3 (M+H)+

Sources & evidence

ORD record
ord-c34cda5ba20a437d97e03ec91416ed22
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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