Trichloroacetyl isocyanate → HCID 86588152, compound

HRID 1828549Notes

Reaction equation

HRID 1828549 reaction equation
[F:1][C:2]1[C:3]([CH2:29][CH2:30][C:31]2[S:32][CH:33]=[C:34]([CH:36]([CH3:38])[CH3:37])[N:35]=2)=[CH:4][C:5]2[N:6]([CH:28]=1)[C:7](=[O:27])[C:8](/[CH:18]=[CH:19]/[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)[N:10]=2.ClC(Cl)(Cl)[C:41]([N:43]=C=O)=[O:42].CO.C(Cl)(Cl)Cl.C([O-])=O.[Na+]>C(OCC)(=O)C>[NH2:43][C:41]([O:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]2[N:10]=[C:5]3[CH:4]=[C:3]([CH2:29][CH2:30][C:31]4[S:32][CH:33]=[C:34]([CH:36]([CH3:38])[CH3:37])[N:35]=4)[C:2]([F:1])=[CH:28][N:6]3[C:7](=[O:27])[C:8]=2/[CH:18]=[CH:19]/[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)=[O:42]

Participants

6

Reactant 4

HCID 76400Trichloroacetyl isocyanateHCID 2723810Sodium Formate2×HCID 21584188Chloroform methanolHCID 86588150HCID 86588150, compound2×

Product 1

HCID 86588152HCID 86588152, compoundYield 137.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl (E)-3-{7-fluoro-2-(3-hydroxypiperidino)-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (48.0 mg, 0.0885 mmol) obtained in Example 156, (M) was dissolved in ethyl acetate (3 ml), added with trichloroacetyl isocyanate (0.052 ml, 0.442 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added with methanol:chloroform (1:10, 10 ml) and concentrated, and the resulting residue was dissolved in a mixed solvent of methanol (3 ml) and distilled water (1 ml), added with sodium formate (12.0 mg, 0.177 mmol) and stirred overnight at room temperature. The solution was further added with sodium formate (12.0 mg, 0.177 mmol), stirred for 5 hours and then concentrated, and the resulting residue was purified by preparative TLC (chloroform:methanol=100:5) to obtain the title compound (71.3 mg, quantitative) as lyophilized product.

Workup

  1. concentrationconcentrated
  2. dissolutionthe resulting residue was dissolved in a mixed solvent of methanol (3 ml)
  3. distillationdistilled water (1 ml)
  4. stirringstirred overnight at room temperature
  5. stirringstirred for 5 hours
  6. concentrationconcentrated
  7. customthe resulting residue was purified by preparative TLC (chloroform:methanol=100:5)

Sources & evidence

ORD record
ord-ffc65b0a625941d1bd4abac445eeb248
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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