Hydrochloric Acid → 4-[(2-methyl-3-oxo-6-propan-2-yl-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-9-yl)amino]-N-(2-morpholin-4-ylethyl)benzamide

HRID 2234284Notes

Reaction equation

HRID 2234284 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1.Cl[C:20]1[N:30]=[C:29]2[C:23]([N:24]([CH3:35])[C:25](=[O:34])[CH2:26][CH2:27][N:28]2[CH:31]([CH3:33])[CH3:32])=[CH:22][N:21]=1.CCO.Cl>CO.O>[CH3:35][N:24]1[C:25](=[O:34])[CH2:26][CH2:27][N:28]([CH:31]([CH3:33])[CH3:32])[C:29]2[C:23]1=[CH:22][N:21]=[C:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)=[O:7])=[CH:17][CH:18]=1)[N:30]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 167819794-amino-N-[2-(morpholin-4-yl)ethyl]benzamideHCID 866175432-Chloro-9-isopropyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one2×

Product 1

HCID 686843074-[(2-methyl-3-oxo-6-propan-2-yl-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-9-yl)amino]-N-(2-morpholin-4-ylethyl)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-amino-N-(2-morpholin-4-ylethyl)benzamide (Buttpark; 188 mg, 0.75 mmol) and 10-chloro-6-methyl-2-propan-2-yl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 76; 160 mg, 0.63 mmol) were heated together in 1:3 EtOH:water (8 ml) in the presence of concentrated hydrochloric acid (126 ul) for 24 hours. The reaction was cooled to ambient temperature and then loaded onto an SCX-2 (5 g) column pre-wet with methanol. The product was eluted with 2M NH3/MeOH and the solvent evaporated to give product as a brown gum. This was purified by reverse phase HPLC to give the title compound a white solid. (125 mg, 42%)

Workup

  1. washThe product was eluted with 2M NH3/MeOH
  2. customthe solvent evaporated
  3. customto give product as a brown gum
  4. customThis was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-03f9700646af41d586d1d0fce79014ed
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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