Glycine methyl ester hydrochloride → Methyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzamido)acetate

HRID 1177449Notes

Reaction equation

HRID 1177449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]1)[N:14]=2)[C:5](O)=[O:6].Cl.[CH3:30][O:31][C:32](=[O:35])[CH2:33][NH2:34]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:21][CH2:22]1)[N:14]=2)[C:5]([NH:34][CH2:33][C:32]([O:31][CH3:30])=[O:35])=[O:6]

Participants

3

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 573944063-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid

Product 1

HCID 67112065Methyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzamido)acetate

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoic acid (0.050 g, 0.13 mmol) and glycine methyl ester hydrochloride (0.019 g, 0.15 mmol), according to Reference S and the general procedure for amide formation afforded methyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzamido)acetate. MS (ESI) m/z: Calculated: 461.1; Observed: 462.0 (M++1).

Sources & evidence

ORD record
ord-149de2b455d8457e8d7cbaceeea98089
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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