Ethanol → HCID 10380703, compound

HRID 2375425Notes

Reaction equation

HRID 2375425 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH3:21])[N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=3)[C:10]([CH3:11])=[C:6]2[C:5]([CH3:22])=[N:4][N:3]=1.[CH3:23][NH2:24].CCO>O>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[C:10]([CH3:11])=[C:6]3[C:7]([C:2]([NH:24][CH3:23])=[N:3][N:4]=[C:5]3[CH3:22])=[C:8]2[CH3:21])=[CH:13][CH:14]=1)[CH3:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 86606406HCID 86606406, compound

Product 1

HCID 10380703HCID 10380703, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a Personal Chemistry Microwave Synthesizer microwave vial was combined 1-chloro-6-(4-ethoxyphenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine (200 mg, 0.64 mmol), MeNH2 (1 mL, 40% in H2O), and EtOH (1 mL). The vial was sealed and heated at 120° C. for 12 min. The reaction mixture was poured into water to afford crude 6-(4-ethoxyphenyl)-N,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazin-1-amine. Purification by reverse phase preparative HPLC using a YMC CombiPrep Pro C1820×100 column (Gradient: 5%-100% Acetonitrile in a H2O+0.1% TFA solution over 10 min, retention time: 6.1 min) afforded pure 6-(4-ethoxyphenyl)-N,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazin-1-amine as a colorless solid: 1H NMR (CDCl3, 500 MHz) δ 7.05-7.12 (m, 4H), 4.16 (q, 2H), 3.20 (s, 3H), 2.69 (s, 3H), 2.43 (s, 3H), 2.39 (s, 3H), 1.51 (t, 3H); MS (ESI) 311 (M+H)+.

Workup

  1. customThe vial was sealed
  2. customto afford crude 6-(4-ethoxyphenyl)-N,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazin-1-amine
  3. customPurification by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-065401163e4443d89c191a3f81df5e31
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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