Methyl azetidine-3-carboxylate hydrochloride → HCID 67111586, compound

HRID 1177447Notes

Reaction equation

HRID 1177447 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26](=O)[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.[NH:30]1[CH2:33][CH:32]([C:34]([O:36][CH3:37])=[O:35])[CH2:31]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:26]([N:30]2[CH2:33][CH:32]([C:34]([O:36][CH3:37])=[O:35])[CH2:31]2)[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

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 59174916HCID 59174916, compound

Product 1

HCID 67111586HCID 67111586, compound

Procedure

Reaction of 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethanone (1.76 g, 4.53 mmol) and methyl azetidine-3-carboxylate hydrochloride (1.03 g, 6.80 mmol) according to reference R and the general procedure for reductive amination gave racemic methyl 1-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)azetidine-3-carboxylate. Separation of enantiomers was accomplished by SFC chromatography (Column: Chiralcel OJ-H (21×250 mm, 5 um)×2; A: Liquid CO2; B: Ethanol (0.2% IPA); Isocratic: 80:20 (A:B); Flow Rate: 70 mL/min; Outlet Pressure: 100 bar) to give (R)-methyl 1-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)azetidine-3-carboxylate and (S)-methyl 1-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)azetidine-3-carboxylate. MS (ESI) m/z: Calculated: 487.2; Observed: 488.1 (M++1).

Sources & evidence

ORD record
ord-e0df09c41f7c4082bb0c0e1746a49b7b
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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