Dimethylamine, hydrochloride → HCID 9848783, compound

HRID 1433078Notes

Reaction equation

HRID 1433078 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([C:25](O)=[O:26])[N:24]=4)[C:15](=[O:28])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:29]=1.[CH3:30][N:31](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:32].[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CNC>CN1CCCC1=O>[CH3:30][N:31]([CH3:32])[C:25]([C:23]1[N:24]=[C:20]([CH2:19][N:16]2[CH2:17][CH2:18][N:13]([S:10]([C:8]3[S:7][C:6]4[CH:29]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[CH:9]=3)(=[O:12])=[O:11])[CH2:14][C:15]2=[O:28])[S:21][CH:22]=1)=[O:26]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 67014565HCID 67014565, compound

Product 1

HCID 9848783HCID 9848783, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl-carboxylic acid (14 mg, 0.03 mmol) in N-methyl-pyrolidinone (0.3 mL) is added TBTU (0.05 mmol) and diisopropylethylamine (0.06 mmol) and dimethylamine hydrochloride (0.06). The reaction is stirred 3 h and an additional aliquot of TBTU, DIEA and amine are added. The reaction is stirred 1 h and the reaction is concentrated and purified by column chromatography (silica, 2% MeOH/EtOAc) to provide 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazole-4-carboxylic acid dimethylamide. 1H NMR (300 MHz, CDCl3) δ 7.87-7.77 (m, 4H), 7.47 (dd, 1H), 4.83 (s, 2H), 3.92 (s, 2H), 3.63-3.60 (m, 2H), 3.47-3.43 (m, 2H), 3.18 (s, 3H), 3.10 (s, 3H); MS (Ion Spray) 499 (M+H)+.

Workup

  1. stirringThe reaction is stirred 1 h
  2. concentrationthe reaction is concentrated
  3. custompurified by column chromatography (silica, 2% MeOH/EtOAc)

Sources & evidence

ORD record
ord-b517f0b0846d449c8897eaa3e42ee4d6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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