Ammonia → HCID 86671548, compound

HRID 1422969Notes

Reaction equation

HRID 1422969 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7]([CH:9]1[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[N:14]=[CH:13][C:12]=2[O:11][CH2:10]1)=O.N>C(O)C>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]1[O:11][CH2:10][CH:9]([C:7]3[N:1]=[C:2]([NH2:4])[S:3][CH:6]=3)[CH2:22][C:21]2=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2723790ThioureaHCID 86671547HCID 86671547, compound

Product 1

HCID 86671548HCID 86671548, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (190 mg, 2.5 mmol, 1.0 eq) is added at room temperature to a stirred solution of 2-bromo-1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-ethanone (850 mg, 2.5 mmol, 1.0 eq) in ethanol (200 mL) and the resulting suspension is heated to reflux for 15 minutes. Then pH of the reaction mixture is adjusted to 8-10 by the addition of a 30% aqueous ammonia solution. Solvent was removed to give the crude product that is purified by preparative HPLC to afford 4-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-thiazol-2-ylamine as a white solid (60 mg, 13% yield).

Workup

  1. temperaturethe resulting suspension is heated
  2. temperatureto reflux for 15 minutes
  3. customSolvent was removed
  4. customto give the crude product that
  5. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-5f984de6e76049c696cffb36c4d0c793
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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