Ethanolamine → HCID 11660819, compound

HRID 215986Notes

Reaction equation

HRID 215986 reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:3]=1.[CH2:25]([CH2:27][NH2:28])[OH:26]>C(Cl)Cl>[C:11]1([C:10]2[C:5]3[C:6](=[N:7][C:2]([NH:28][CH2:27][CH2:25][OH:26])=[CH:3][C:4]=3[NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11681859HCID 11681859, compound

Product 1

HCID 11660819HCID 11660819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of (6-chloro-3-phenyl-thieno[2,3-b]pyridin-4-yl)-pyridin-2-ylmethyl-amine (20 mg, 0.57 mmol) and ethanolamine (1 ml) were heated to 200° C. in the microwave and maintained at this temperature for 90 min. On cooling, the reaction mixture was poured into DCM (50 ml) and washed with water (2×50 ml), dried (Na2SO4), and concentrated. The residue was purified on silica (ethyl acetate, 100%) to give 2-{3-phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-ylamino}-ethanol as a white solid. Yield=18 mg (83.9%).

Workup

  1. temperaturemaintained at this temperature for 90 min
  2. temperatureOn cooling
  3. washwashed with water (2×50 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified on silica (ethyl acetate, 100%)

Sources & evidence

ORD record
ord-a3eeb6fde22a41a3b080c17fd61728f7
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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