1-Methylpiperazine → HCID 136377200, compound

HRID 624546Notes

Reaction equation

HRID 624546 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[CH:11]=[C:10]([CH3:13])[S:9][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][C:16]([C:18]#[N:19])=[CH:17][C:5]=2[N:4]=1.[CH3:20][N:21]1[CH2:26][CH2:25]N[CH2:23][CH2:22]1>CS(C)=O.C1(C)C=CC=CC=1>[CH3:13][C:10]1[S:9][C:8]2[NH:7][C:6]3[CH:14]=[CH:15][C:16]([C:18]#[N:19])=[CH:17][C:5]=3[N:4]=[C:3]([N:2]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 136377198HCID 136377198, compound

Product 1

HCID 136377200HCID 136377200, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 10-amino-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene-7-carbonitrile hydrochloride, prepared as described in the previous step, (0.6 g) in DMSO (6 mL) and toluene (6 mL), was added 1-methylpiperazine (4 mL). The mixture was heated in a 130° C. oil bath for 17 hours. The solution was concentrated, diluted with ethyl acetate (50 mL), washed with water (20 mL) and brine (20 mL), and then concentrated. The solid was dissolved in dichloromethane (10 mL) and treated with saturated sodium bicarbonate solution. The title compound was collected as a light yellow precipitate, washed with water and dichloromethane, dried, and used in the next step without additional purification. LC-MS: m/z 338 (M+1). 1H NMR (CD3OD, 400 MHz): δ (ppm) 7.19-7.15 (m, 2H), 6.74 (d, 1H), 6.37 (s, 1H), 3.51 (m, 4H), 2.53 (m, 4H), 2.34 (s, 3H), 2.32 (s, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water (20 mL) and brine (20 mL)
  4. concentrationconcentrated
  5. dissolutionThe solid was dissolved in dichloromethane (10 mL)
  6. additiontreated with saturated sodium bicarbonate solution
  7. customThe title compound was collected as a light yellow precipitate
  8. washwashed with water and dichloromethane
  9. customdried
  10. customused in the next step without additional purification

Sources & evidence

ORD record
ord-8703ad7d687d450092b3cd5af6ec396a
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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