2-Aminothiazole → HCID 59132753, compound

HRID 1993038Notes

Reaction equation

HRID 1993038 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:22]#[C:23][CH3:24])[CH2:18][C:19](O)=[O:20])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.C1COCC1.[NH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1>O>[S:44]1[CH:45]=[CH:46][N:47]=[C:43]1[NH:42][C:19](=[O:20])[CH2:18][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:12][CH:13]=1)[C:22]#[C:23][CH3:24]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 8028TetrahydrofuranHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 42603138HCID 42603138, compound

Product 1

HCID 59132753HCID 59132753, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A pear-shaped flask was charged with a stir bar, compound 12 (50 mg, 0.154 mmol), carbonyl diimidazole (25 mg, 0.154 mmol) and THF (4 mL). The mixture was refluxed for 1 hour, and 2-amino thiazole (16 mg, 0.154 mmol) was then added. The reaction was refluxed for 48 hours, poured into water and extracted with ethyl acetate. The organic layer was concentrated and the resulting residue was purified via HPLC to yield 1.0 mg (2%) of 3-[4-(4-Methoxy-benzyloxy)-phenyl]-hex-4-ynoic acid thiazol-2-ylamide (24) as a film. 1H NMR (400 MHz) (acetone-d6) δ 7.39 (4H, m), 7.11 (1H, s), 6.95 (3H, m), 5.03 (2H, s), 3.82 (3H, s), 2.95 (2H, m), 1.79 (3H, s).

Workup

  1. additionA pear-shaped flask was charged with a stir bar
  2. temperatureThe mixture was refluxed for 1 hour
  3. temperatureThe reaction was refluxed for 48 hours
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe resulting residue was purified via HPLC

Sources & evidence

ORD record
ord-fb6c36b335f34de5bbb45daad1576a3d
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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