Methyl azetidine-3-carboxylate hydrochloride → Methyl 1-(4-(5-(1-cyclobutylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

HRID 1177594Notes

Reaction equation

HRID 1177594 reaction equation
[CH:1]1([C:5]2([C:8]3[N:13]=[C:12]4[S:14][C:15]([C:17]5[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=5[F:25])=[N:16][C:11]4=[CH:10][CH:9]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl.[NH:27]1[CH2:30][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:28]1>>[CH:1]1([C:5]2([C:8]3[N:13]=[C:12]4[S:14][C:15]([C:17]5[CH:24]=[CH:23][C:20]([CH2:21][N:27]6[CH2:30][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:28]6)=[CH:19][C:18]=5[F:25])=[N:16][C:11]4=[CH:10][CH:9]=3)[CH2:6][CH2:7]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387264-(5-(1-Cyclobutylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzaldehyde

Product 1

HCID 67111788Methyl 1-(4-(5-(1-cyclobutylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

Procedure

Reaction of 4-(5-(1-cyclobutylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzaldehyde (66.2 mg, 0.188 mmol) and methyl azetidine-3-carboxylate hydrochloride (42.7 mg, 0.282 mmol) according to Reference R and the general procedure for reductive amination to give methyl 1-(4-(5-(1-cyclobutylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate as a white solid. MS (ESI) m/z: Calculated: 451.2; Observed: 451.9 (M++1).

Sources & evidence

ORD record
ord-6312fb8934c6424fa5d2f6103e8963f3
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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