3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde → HCID 67111706, compound

HRID 1177422Notes

Reaction equation

HRID 1177422 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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)[CH:5]=O.C(O)(=O)C.[OH:32][C:33]1([C:37]([O:39][CH3:40])=[O:38])[CH2:36][NH:35][CH2:34]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:35]2[CH2:36][C:33]([OH:32])([C:37]([O:39][CH3:40])=[O:38])[CH2:34]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:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2

Participants

3

Reactant 2

HCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehydeHCID 67112000Methyl 3-hydroxyazetidine-3-carboxylate acetate

Product 1

HCID 67111706HCID 67111706, compound

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde (0.209 g, 0.56 mmol) and methyl 3-hydroxyazetidine-3-carboxylate acetate (0.14 g, 0.73 mmol) according to Reference R and general procedure for reductive amination afforded methyl 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)-3-hydroxyazetidine-3-carboxylate. MS (ESI) m/z: Calculated: 489.2; Observed: 490.0 (M++1).

Sources & evidence

ORD record
ord-04f04e08aece497e9a2ff19610d9085e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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