3-azetidinecarboxylic Acid → 1-(4-(5-(1-Phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine-3-carboxylic acid

HRID 1177560Notes

Reaction equation

HRID 1177560 reaction equation
[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=5)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:27]1[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]1>>[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[CH:21][C:22]([CH2:23][N:27]6[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]6)=[CH:25][CH:26]=5)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 931923-azetidinecarboxylic AcidHCID 866387254-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 445996851-(4-(5-(1-Phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine-3-carboxylic acid

Procedure

Reaction of 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (38.9 mg, 0.109 mmol) and azetidine-3-carboxylic acid (55 mg, 0.546 mmol) according to Reference R and the general procedure for reductive amination to give 1-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine-3-carboxylic acid as a white solid. MS (ESI) m/z: Calculated: 441.2; Observed: 442.1 (M++1).

Sources & evidence

ORD record
ord-1927a820dd2a42ec8205774528961b1a
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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