L-Proline → HCID 44600009, compound

HRID 1177583Notes

Reaction equation

HRID 1177583 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.[NH:28]1[CH2:35][CH2:34][CH2:33][C@H:29]1[C:30]([OH:32])=[O:31]>>[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:28]1[CH2:35][CH2:34][CH2:33][C@H:29]1[C:30]([OH:32])=[O:31]

Participants

3

Reactant 2

HCID 145742L-ProlineHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 44600009HCID 44600009, compound

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (101.1 mg, 0.270 mmol) and L-(−)-proline (93.3 mg, 0.810 mμmol) according to Reference R and the general procedure for reductive amination to give (S)-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)pyrrolidine-2-carboxylic acid as a light yellow solid. MS (ESI) m/z: Calculated: 473.2; Observed: 474.2 (M++1).

Sources & evidence

ORD record
ord-d2ab1b02c9214919847d3edea02b90db
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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