Thiourea → HCID 44601108, compound

HRID 1177466Notes

Reaction equation

HRID 1177466 reaction equation
ClCC([NH:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[C:22]([N:23]=2)=[CH:21][CH:20]=[C:19]([C:24]2([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:26][CH2:25]2)[N:18]=3)=[C:11]([F:33])[CH:10]=1)([CH3:8])[CH3:7])=O.NC(N)=S>C(O)C.C(O)(=O)C.C(Cl)Cl>[F:33][C:11]1[CH:10]=[C:9]([C:6]([NH2:5])([CH3:7])[CH3:8])[CH:14]=[CH:13][C:12]=1[C:15]1[S:16][C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]1([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:25][CH2:26]1)[N:18]=2

Participants

6

Reactant 2

HCID 2723790ThioureaHCID 67112027HCID 67112027, compound

Product 1

HCID 44601108HCID 44601108, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-N-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-yl)acetamide (0.51 g, 1.0 mmol) in ethanol (10 mL) and acetic acid (2 mL) was added thiourea (0.12 g, 1.58 mmol). The reaction mixture was heated to reflux for 18 hours. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. ISCO purification with 1% to 10% MeOH/CH2Cl2 afforded a crude crop of the desired product. Trituration with CH2Cl2 afforded 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-propan-2-amine as a white amorphous solid. MS (ESI) m/z: Calculated: 403.2; Observed: 404.1 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customISCO purification with 1% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-aec24e8d17a1467fa0f49a5241ddf4a1
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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