3-Amino-1-propanol → HCID 11198662, compound

HRID 1951176Notes

Reaction equation

HRID 1951176 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[N:10][C:9]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH2:21][CH2:22][CH2:23][CH2:24][OH:25]>>[CH3:20][C:9]1[N:10]=[C:11]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[S:12][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[CH:7]=1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 11301149[5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

Product 1

HCID 11198662HCID 11198662, compound

Conditions

Temperature
150 °C

Procedure

[5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine (Example 2b, 0.077 g, 0.254 mmol) is suspended in 3-amino-propanol (3 ml) and heated to 150° C. using microwave heating (Prolabo Synthewave™ s402 microwave oven). After 1 hour, the reaction mixture is concentrated in vacuo and diluted with water (50 ml). The aqueous is extracted with ethyl acetate (2×100 ml). The combined organic extract is dried (MgSO4) and concentrated to afford the titled compound which is purified by filtration and recrystallised from dichloromethane.

Workup

  1. temperatureheating (Prolabo Synthewave™ s402 microwave oven)
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. additiondiluted with water (50 ml)
  4. extractionThe aqueous is extracted with ethyl acetate (2×100 ml)
  5. extractionThe combined organic extract
  6. dry with materialis dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4628109f588949369994beb3f94932b2
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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