2-Aminothiazole → HCID 18381673, compound

HRID 2268889Notes

Reaction equation

HRID 2268889 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[N:4][N:3]=1.[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:22][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:21])[C:15]=1[CH2:14][C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:2]([NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)=[N:3][N:4]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 18381673HCID 18381673, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

At 100° C. a solution of 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (0.5 g, 1.41 mmoles), prepared as described in example 45, 2-aminothiazole (0.424 g, 4.23 mmoles), triethylamine (0.59 ml, 4.23 mmoles), palladium acetate (16 mg, 0.07 mmoles) and triphenylphosphine (56 mg, 0.21 mmoles) was stirred under N2. After 20 hours the mixture was poured into water/ice and extracted more times with CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give a solid which was flash chromatographed (eluent: hexane/ethyl acetate 7:3) yielding 0.24 g of the title compound (yield: 50%). m.p.: 218-220° C.

Workup

  1. extractionextracted more times with CH2Cl2
  2. washThe organic phase was washed with water, anhydrified
  3. concentrationconcentrated
  4. customto give a solid which
  5. customchromatographed (eluent: hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-35dd7773e7d34d8dbe275a90c741c77a
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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