1-Hydroxybenzotriazole → HCID 57568673, compound

HRID 1845718Notes

Reaction equation

HRID 1845718 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]1(=[O:25])[N:17]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)[C:16](=[O:24])[CH:15]=[CH:14]1.ON1C2C=CC=CC=2N=N1.[NH:36]1[CH2:41][CH2:40][CH:39]([CH2:42][C:43]2[N:44]([CH2:57][CH2:58][CH3:59])[N:45]=[C:46]3[C:55]=2[C:54]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[N:48]=[C:47]3[NH2:56])[CH2:38][CH2:37]1>CN(C=O)C.O>[NH2:56][C:47]1[C:46]2=[N:45][N:44]([CH2:57][CH2:58][CH3:59])[C:43]([CH2:42][CH:39]3[CH2:40][CH2:41][N:36]([C:21](=[O:23])[CH2:20][CH2:19][CH2:18][N:17]4[C:13](=[O:25])[CH:14]=[CH:15][C:16]4=[O:24])[CH2:37][CH2:38]3)=[C:55]2[C:54]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[N:48]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 34049044-Maleimidobutyric AcidHCID 68922921HCID 68922921, compound

Product 1

HCID 57568673HCID 57568673, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.266 g, 1.39 mmol) was added to a mixture of 4-maleimidobutyric acid (0.254 g, 1.39 mmol) and 1-hydroxybenzotriazole (0.187 g, 1.39 mmol) in DMF (13 mL). The mixture was stirred for 1 hour, then 1-(piperidin-4-ylmethyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (0.450 g, 1.39 mmol) was added. The mixture was stirred for 1 hour, then water (60 mL) was added, and the mixture was stirred an additional hour. The aqueous layer was extracted with ethyl acetate (2×75 mL) and dichloromethane (2×75 mL). The organic layers were combined, washed with water (2×100 mL) and brine, and then concentrated under reduced pressure. The resulting residue was purified by HPFC on silica gel (gradient elution with 2-20% CMA in chloroform) to provide 0.251 g of 1-(4-{4-[(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-1-yl}-4-oxobutyl)-1H-pyrrole-2,5-dione as a yellow foam. Anal. Calcd for C27H32N6O3.0.75H2O: C, 64.36; H, 6.68; N, 16.53. Found: C, 64.59; H, 6.73; N, 16.74.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred an additional hour
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×75 mL) and dichloromethane (2×75 mL)
  4. washwashed with water (2×100 mL) and brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by HPFC on silica gel (gradient elution with 2-20% CMA in chloroform)

Sources & evidence

ORD record
ord-27fb76f9a07440eeaf2c991df6b7dec5
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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