HCID 67431982, compound → HCID 58456278, compound

HRID 410606Notes

Reaction equation

HRID 410606 reaction equation
C(OC([N:8]([C:29]1[N:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=1)[C:9]1[CH:10]=[C:11]([C:16]2[S:20][C:19]([CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[N:18][CH:17]=2)[CH:12]=[C:13]([CH3:15])[CH:14]=1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O.ClCCCl>[CH3:27][C:22]([CH3:28])([CH2:21][C:19]1[S:20][C:16]([C:11]2[CH:10]=[C:9]([NH:8][C:29]3[N:34]=[C:33]([C:35]([F:38])([F:36])[F:37])[CH:32]=[CH:31][N:30]=3)[CH:14]=[C:13]([CH3:15])[CH:12]=2)=[CH:17][N:18]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 1

HCID 67431982HCID 67431982, compound

Product 1

HCID 58456278HCID 58456278, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Step 2 (390 mg, 0.708 mmol) was dissolved in CH2Cl2 (8 mL)/TFA (2 mL) and stirred at room temperature for 90 min. The reaction was subsequently diluted with 1,2-DCE and evaporated to dryness. The residue was redissolved in EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-50% ethyl acetate in hexanes) afforded 293 mg (92%) of methyl 2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanoate as a yellow gum. MS ESI: [M+H]+ m/z 451.0. 1H NMR (600 MHz, DMSO-d6) δ 10.23 (s, 1H), 8.80 (d, J=4.9, 1H), 8.00-7.88 (m, 2H), 7.43 (s, 1H), 7.25 (d, J=4.9, 1H), 7.13 (s, 1H), 3.61 (s, 3H), 3.19 (s, 2H), 2.29 (s, 3H), 1.18 (s, 6H). rhSYK activity=+++

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was redissolved in EtOAc
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8742dd35024a4541aa32c0d85993a2d3
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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