Dichloromethane → HCID 24771573, compound

HRID 1429598Notes

Reaction equation

HRID 1429598 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.BrC1N=[C:24]([C:26]([OH:28])=O)C=CC=1.[CH:29](N1CCNCC1)([CH3:31])[CH3:30].[ClH:38].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH2:69]([Cl:71])Cl>O>[Cl:71][C:69]1[CH:24]=[C:26]([CH:31]=[CH:29][C:30]=1[Cl:38])[O:28][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 7

HCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57425298HCID 57425298, compound

Product 1

HCID 24771573HCID 24771573, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-Bromo-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone. To a solution of 6-bromo-pyridine-2-carboxylic acid (100.00 mg, 0.50 mmol) in DCM (5.0 mL) was added 1-isopropylpiperazine (95.20 mg, 0.74 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC; 189.78 mg, 0.99 mmol), 1-hydroxybenzotriazole (HOBt; 133.78 mg, 0.99 mmol), and iPr2NEt (0.86 mL, 4.95 mmol). After 18 h at rt, the mixture was diluted with water and extracted with DCM. Purification by FCC provided the desired product (83.0 mg, 54%). MS (ESI): mass calcd. for C13H18BrN3O, 311.06; m/z found, 312.2 [M+H]+. 1H NMR (CDCl3): 7.69-7.59 (m, 2H), 7.56-7.52 (m, 1H), 3.84-3.76 (m, 2H), 2.79-2.68 (m, 1H), 2.62 (t, J=5.1 Hz, 2H), 2.53 (t, J=5.1 Hz, 2H), 1.06 (d, J=6.5 Hz, 6H). Assay 1 (Human H3): K=1400 nM.

Workup

  1. extractionextracted with DCM
  2. customPurification by FCC

Sources & evidence

ORD record
ord-6d060ddac2154524b54510d2ccaf1aea
Source dataset
uspto-grants-2015_01
Patent number
US08940731B2

Reaction notes

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