Diisopropylethylamine → Methyl 1-((3-amino-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

HRID 1177521Notes

Reaction equation

HRID 1177521 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:28][N:29]2[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]2)[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)([O-])=O.C(N(CC)C(C)C)(C)C.[H][H]>[Pd].O>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:28][N:29]2[CH2:30][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:32]2)[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 67112881HCID 67112881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67111429Methyl 1-((3-amino-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A slurry of methyl 1-((3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate (0.390 g, 0.78 mmol) and 10% palladium on carbon, 50% water, (0.41 g) and N,N-diisopropylethylamine (0.27 mL, 1.6 mmol) was treated with a hydrogen balloon and stirred rapidly for 2 h, then was flushed with nitrogen, filtered through celite, rinsing with MeOH/DCM. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography 40 g, 20-100% EA/hexanes to give methyl 1-((3-amino-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as a yellow solid. MS (ESI) m/z: Calculated: 470.2; Observed: 470.8 (M++1).

Workup

  1. customwas flushed with nitrogen
  2. filtrationfiltered through celite
  3. washrinsing with MeOH/DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by silica gel chromatography 40 g, 20-100% EA/hexanes

Sources & evidence

ORD record
ord-d57a06d135f145688a34361377f5e2b9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…