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

HRID 1177600Notes

Reaction equation

HRID 1177600 reaction equation
[F:1][C:2]1([F:27])[CH2:5][CH:4]([C:6]2([C:9]3[N:14]=[C:13]4[S:15][C:16]([C:18]5[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=5[F:26])=[N:17][C:12]4=[CH:11][CH:10]=3)[CH2:8][CH2:7]2)[CH2:3]1.Cl.[NH:29]1[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]1>>[F:27][C:2]1([F:1])[CH2:3][CH:4]([C:6]2([C:9]3[N:14]=[C:13]4[S:15][C:16]([C:18]5[CH:25]=[CH:24][C:21]([CH2:22][N:29]6[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]6)=[CH:20][C:19]=5[F:26])=[N:17][C:12]4=[CH:11][CH:10]=3)[CH2:7][CH2:8]2)[CH2:5]1

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387274-(5-(1-(3,3-Difluorocyclobutyl)cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzaldehyde

Product 1

HCID 67112099Methyl 1-(4-(5-(1-(3,3-difluorocyclobutyl)cyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

Procedure

Reaction of 4-(5-(1-(3,3-difluorocyclobutyl)cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzaldehyde (112.0 mg, 0.288 mmol) and methyl azetidine-3-carboxylate hydrochloride (65.6 mg, 0.433 mmol) according to Reference R and the general procedure for reductive amination gave methyl 1-(4-(5-(1-(3,3-difluorocyclobutyl)cyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate as a white solid. MS (ESI) m/z: Calculated: 487.2; Observed: 487.8 (M++1).

Sources & evidence

ORD record
ord-4320f942f1944798b96912142c153e60
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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