Diisopropylethylamine → HCID 67112881, compound

HRID 1177520Notes

Reaction equation

HRID 1177520 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[C:13]([C:18]2([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:20][CH2:19]2)[N:12]=3)=[C:5]([N+:27]([O-:29])=[O:28])[CH:4]=1.Cl.[NH:31]1[CH2:34][CH:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CC(=O)OCC>[N+:27]([C:5]1[CH:4]=[C:3]([CH2:2][N:31]2[CH2:34][CH:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]2)[CH:8]=[CH:7][C:6]=1[C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([C:18]1([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:20][CH2:19]1)[N:12]=2)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 671118432-(4-(Bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine

Product 1

HCID 67112881HCID 67112881, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-(bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine (0.363 g, 0.778 mmol), methyl azetidine-3-carboxylate hydrochloride (0.354 g, 2.34 mmol), N,N-diisopropylethylamine (0.812 mL, 4.67 mmol) in 3 mL DMF was heated in a sealed vial to 80° C. for 1 h. The reaction mixture was cooled and allowed to stand overnight. In the morning the reaction mixture was treated with ice, sat'd aq. NaHCO3, and EA. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography, 40 g, 0-10% MeOH/DCM gave methyl 1-((3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as a yellow oil. MS (ESI) m/z: Calculated: 500.2; Observed: 500.7 (M++1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionIn the morning the reaction mixture was treated with ice
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography, 40 g, 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-79297f7f76a8489eb1ff72f9a8f3e85f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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