2-Chloronicotinic acid → HCID 86596148, compound

HRID 2222935Notes

Reaction equation

HRID 2222935 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=[O:5].[C:11]([CH2:13][NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([S:33][CH2:34][CH2:35][NH2:36])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:16])#[N:12].C(N(C(C)C)CC)(C)C>O1CCCC1>[S:24]([OH:25])(=[O:26])(=[O:5])[CH3:27].[C:11]([CH2:13][NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([S:33][CH2:34][CH2:35][NH:36][C:3]2[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=2)=[CH:29][CH:28]=1)(=[O:25])=[O:26])=[O:16])#[N:12]

Participants

5

Reactant 3

HCID 762582-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 10272041HCID 10272041, compound

Product 1

HCID 86596148HCID 86596148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloronicotinic acid (20 mg, 0.112 mmol), and trans-N-cyanomethyl-2-[4-(aminoethylsulfanyl)benzenesulfonylmethyl]cyclohexanecarboxamide (50 mg, 0.102 mmol) in tetrahydrofuran (1 mL) was added diisopropylethylamine (71 μL, 0.407 mmol). The reaction mixture was stirred overnight at room temperature, then purified directly on a short plug of silica gel (0-10% methanol/dichloromethane) to give the title compound. MS [ESI, (M+H)+] m/z 535 amu, MS [ESI, (M+Na)+] m/z=557 amu.

Workup

  1. custompurified directly on a short plug of silica gel (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-1975fa5ee3144a4393011df6eca2ff70
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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