3-Hydroxyazetidine hydrochloride → 1-((3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)azetidin-3-ol

HRID 1177488Notes

Reaction equation

HRID 1177488 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.Cl.[OH:29][CH:30]1[CH2:33][NH:32][CH2:31]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:32]2[CH2:33][CH:30]([OH:29])[CH2:31]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 27592903-Hydroxyazetidine hydrochlorideHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 446014431-((3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)azetidin-3-ol

Procedure

Synthesized from 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (0.500 g, 1.34 mmol) and 3-hydroxyazetidine hydrochloride (0.293 g, 2.67 mmol) according to the general procedure for reductive amination to afford 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidin-3-ol as a pale yellow solid. MS (ESI) m/z: Calculated: 431.2; Observed: 432.1 (M++1).

Sources & evidence

ORD record
ord-ca2d67bd6e0b42e595ae378f92830fbc
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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