Azetidine → 2-(4-(Azetidin-1-ylmethyl)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

HRID 1177557Notes

Reaction equation

HRID 1177557 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[C:14]([C:19]2([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:21][CH2:20]2)[N:13]=3)[CH:7]=[C:6]([CH3:28])[C:3]=1[CH:4]=O.[NH:29]1[CH2:32][CH2:31][CH2:30]1>>[N:29]1([CH2:4][C:3]2[C:6]([CH3:28])=[CH:7][C:8]([C:10]3[S:11][C:12]4[C:17]([N:18]=3)=[CH:16][CH:15]=[C:14]([C:19]3([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:20][CH2:21]3)[N:13]=4)=[CH:9][C:2]=2[CH3:1])[CH2:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 866387112,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Product 1

HCID 445996842-(4-(Azetidin-1-ylmethyl)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Procedure

Reaction of 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (29.3 mg, 76 μmol) and azetidine (18 μL, 267 μmol) according to Reference R and the general procedure for reductive amination gave 2-(4-(azetidin-1-ylmethyl)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a light yellow solid. MS (ESI) m/z: Calculated: 425.2; Observed: 426.1 (M++1). 3-(Azetidin-1-yl)-N-(2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)propan-1-amine was also obtained from this reaction as a light yellow solid. MS (ESI) m/z: Calculated: 482.3; Observed: 483.2 (M++1).

Sources & evidence

ORD record
ord-ab37f9d9cc6841a0aa9410fe43fe104a
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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