4-Cyanobenzaldehyde → 4-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile

HRID 1177558Notes

Reaction equation

HRID 1177558 reaction equation
[NH2:1][C:2]1[C:3](=[S:17])[NH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH:18]([C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)=O.NC1C(=S)NC=CC=1>>[C:11]1([C:8]2([C:5]3[N:4]=[C:3]4[S:17][C:18]([C:20]5[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=5)=[N:1][C:2]4=[CH:7][CH:6]=3)[CH2:10][CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 54631813-Aminopyridine-2-thiolHCID 591748363-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Product 1

HCID 671129224-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile

Procedure

Reaction of 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (55.6 mg, 229 μmol) and 4-formylbenzonitrile (29 mg, 218 μmol) according to Reference U and the general procedure for oxidative condensation of 3-aminopyridine-2-thione with aryl aldehydes gave 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile as a light yellow solid. MS (ESI) m/z: Calculated: 353.1; Observed: 354.1 (M++1).

Sources & evidence

ORD record
ord-4bf1319764b04bccba913de11dc0df26
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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