Acetic Acid → HCID 67112027, compound

HRID 1177465Notes

Reaction equation

HRID 1177465 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26](O)([CH3:28])[CH3:27])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[Cl:30][CH2:31][C:32]#[N:33].C(O)(=[O:36])C.S(=O)(=O)(O)O>C(Cl)Cl>[Cl:30][CH2:31][C:32]([NH:33][C:26]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:18][CH2:19]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1)([CH3:28])[CH3:27])=[O:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 67112059HCID 67112059, compound

Product 1

HCID 67112027HCID 67112027, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-ol (0.715 g, 1.77 mmol) at 0° C. under argon was added 2-chloroacetonitrile (0.67 mL, 10.6 mmol), followed by acetic acid (1.4 mL) and sulfuric acid (0.90 mL). The resulting yellow reaction mixture was warmed to room temperature and stirred for 4 hours, during which LC-MS indicated completion of reaction. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution and brine; dried (MgSO4). The organic layer was filtered and concentrated in vacuo. ISCO purification with 10% to 40% EtOAc/Hexanes afforded 2-chloro-N-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-yl)acetamide as a white amorphous solid. MS (ESI) m/z: Calculated: 480.0; Observed: 481.1 (M++1).

Workup

  1. customcompletion of reaction
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialdried (MgSO4)
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated in vacuo
  6. customISCO purification with 10% to 40% EtOAc/Hexanes

Sources & evidence

ORD record
ord-4e37cf11e60f4690982e02ab83e854b8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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