3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde → HCID 44600161, compound

HRID 1177585Notes

Reaction equation

HRID 1177585 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.FC(F)(F)C(O)=O.[NH:35]1[CH2:38][CH:37]([CH2:39][C:40]([OH:42])=[O:41])[CH2:36]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:35]1[CH2:38][CH:37]([CH2:39][C:40]([OH:42])=[O:41])[CH2:36]1

Participants

3

Reactant 2

HCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehydeHCID 671126063-Azetidineacetic acid trifluoroacetate

Product 1

HCID 44600161HCID 44600161, compound

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (100.0 mg, 0.267 mmol) and 2-(azetidin-3-yl)acetic acid trifluoroacetic acid (88.1 mg, 0.384 mmol) according to Reference R and the general procedure for reductive amination to give 2-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidin-3-yl)acetic acid as a tan solid. MS (ESI) m/z: Calculated: 473.2; Observed: 474.1 (M++1).

Sources & evidence

ORD record
ord-334e2cd80a9f43a8986d2f25fe7d74b5
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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