1-Hydroxybenzotriazole → HCID 57425298, compound

HRID 474195Notes

Reaction equation

HRID 474195 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:17]2[CH2:18][CH2:19][N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][CH2:16]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57425298HCID 57425298, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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): Ki=1400 nM.

Workup

  1. extractionextracted with DCM
  2. customPurification by FCC

Sources & evidence

ORD record
ord-95fe8fca3c274cc99a7cac19c5df121d
Source dataset
uspto-grants-2014_01
Patent number
US08637520B2

Reaction notes

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