2-Aminothiazole → HCID 58063581, compound

HRID 2035715Notes

Reaction equation

HRID 2035715 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[N:16][N:17]([CH:19]3[CH2:25][CH2:24][C:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=4[N:21]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:20]3=[O:35])[CH:18]=2)=[CH:10][C:9]=1[O:36][CH3:37].CC(C)([O-])C.[K+].C1COCC1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:37][O:36][C:9]1[CH:10]=[C:11]([C:14]2[N:15]=[N:16][N:17]([CH:19]3[CH2:25][CH2:24][C:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=4[N:21]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:20]3=[O:35])[CH:18]=2)[CH:12]=[CH:13][C:8]=1[NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 8028TetrahydrofuranHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 66683035HCID 66683035, compound

Product 1

HCID 58063581HCID 58063581, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1,3-thiazol-2-amine (5.54 mg, 0.055 mmol 3-[4-(4-iodo-3-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (20 mg, 0.037 mmol), potassium tert-butoxide 1M in THF (36.9 μL, 0.037 mmol), BINAP (4.59 mg, 0.008 mmol), and palladium acetate (1.66 mg, 0.008 mmol) were combined in a μwave vial and dissolved in DMF (738 μl). The reaction was microwaved at 180° C. for 5 minutes. The reaction mixture was filtered, and the solvent was removed in vacuo. Analytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% Formic Acid. Lyophilisation afforded 3-{4-[3-methoxy-4-(1,3-thiazol-2-ylamino)phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one.

Workup

  1. customThe reaction was microwaved at 180° C. for 5 minutes
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customAnalytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18)
  5. washeluting with acetonitrile/water+0.05% Formic Acid

Sources & evidence

ORD record
ord-b3929e443e674de79fbba2c6a363b9e3
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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