1-Hydroxybenzotriazole → 3-Amino-4-bromo-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

HRID 335283Notes

Reaction equation

HRID 335283 reaction equation
CN(C)CCN=C=NCCC.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Br:22])[C:16]([OH:18])=O.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:36][NH2:37])[CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Br:22])[C:16]([NH:37][CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:27]1[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]1)=[O:18]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27955682-(4-Methyl-1-piperazinyl)benzenemethanamineHCID 34187523-Amino-4-Bromobenzoic AcidHCID 86695678N1,N1-dimethyl-N2-((propylimino)methylene)ethane-1,2-diamine

Product 1

HCID 866956773-Amino-4-bromo-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N1,N1-dimethyl-N2-((propylimino)methylene)ethane-1,2-diamine (0.70 ml, 3.99 mmol) was added to a stirred solution/suspension of 3-amino-4-bromobenzoic acid (719 mg, 3.33 mmol), (2-(4-methylpiperazin-1-yl)phenyl)methanamine (820 mg, 3.99 mmol) and HOBt (140 mg, 1.0 mmol) in dry DCM (20 ml) under argon. After 24 hrs the reaction mixture was diluted with DCM and washed several times with water. The solvent was removed in vacuo and the resulting yellow oil was triturated with DCM/diethyl to give a yellow crystalline powder;

Workup

  1. washwashed several times with water
  2. customThe solvent was removed in vacuo
  3. customthe resulting yellow oil was triturated with DCM/diethyl
  4. customto give a yellow crystalline powder

Sources & evidence

ORD record
ord-af0775104a0a4395ada3c99c99167468
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

Loading…