1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 56657856, compound

HRID 1914765Notes

Reaction equation

HRID 1914765 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([NH:17][C:18]4[CH:23]=[C:22]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH:21]=[CH:20][C:19]=4[O:31][C:32]([F:35])([F:34])[F:33])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:36]([NH2:38])=[O:37])=[N:5]1.C1CCN2C(=NCCC2)CC1>O>[CH3:30][N:27]1[CH2:28][CH2:29][N:24]([C:22]2[CH:21]=[CH:20][C:19]([O:31][C:32]([F:35])([F:34])[F:33])=[C:18]([NH:17][C:13]3[N:12]=[CH:11][C:10]4[CH2:9][CH2:8][C:7]5[C:6]([C:36]([NH2:38])=[O:37])=[N:5][N:4]([CH:3]=[CH2:2])[C:16]=5[C:15]=4[N:14]=3)[CH:23]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 56681780HCID 56681780, compound

Product 1

HCID 56657856HCID 56657856, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2-chloro-ethyl)-8-[5-(4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (350 mg, 0.63 mmol) and DBU (3.5 mL) was heated to 80° C. for 1 h. After cooling the reaction mixture was poured into water and filtered. The crude solid was purified by flash chromatography on silica gel (eluant: DCM/MeOH 95/5) to afford 234 mg (71% yield) of the title compound.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationfiltered
  3. customThe crude solid was purified by flash chromatography on silica gel (eluant: DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-1f4ba5f6a692495a88628974b4814b03
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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