L-Azetidine-2-carboxylic acid → HCID 44600008, compound

HRID 1177581Notes

Reaction equation

HRID 1177581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=O.[CH2:28]1[C@@H:31]([C:32]([OH:34])=[O:33])[NH:30][CH2:29]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2)[CH2:5][N:30]1[CH2:29][CH2:28][C@H:31]1[C:32]([OH:34])=[O:33]

Participants

3

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 44600008HCID 44600008, compound

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (93.3 mg, 0.249 mmol) and L-azetidine-2-carboxylic acid (76 mg, 0.748 mμmol) according to Reference R and the general procedure for reductive amination gave (S)-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-azetidine-2-carboxylic acid as a light yellow solid. MS (ESI) m/z: Calculated: 459.1; Observed: 460.0 (M++1).

Sources & evidence

ORD record
ord-31263fb2dafa48dda533a851f8eabe12
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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