1-Hydroxybenzotriazole → HCID 11617900, compound

HRID 646424Notes

Reaction equation

HRID 646424 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.[NH:49]1[CH2:53][CH2:52][CH2:51][C@H:50]1[CH2:54][N:55]1[CH2:59][CH2:58][CH2:57][CH2:56]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:49]1[CH2:53][CH2:52][CH2:51][CH:50]1[CH2:54][N:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1)=[O:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59264698HCID 59264698, compound

Product 1

HCID 11617900HCID 11617900, compoundYield 10%

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 (248 mg, 1.0 mmol), EDC-HCl (287 mg, 1.5 mmol), HOBt (203 mg, 1.5 mmol), DIEA (0.43 mL, 2.5 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (131 mg, 0.85 mmol) to give the title compound (30 mg, 10% yield). MS (ES+) 384.2 (M+H)+

Sources & evidence

ORD record
ord-8148e4aa34e7474faf21663d3cf723ff
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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