Trichloroacetonitrile → HCID 59026804, compound

HRID 658372Notes

Reaction equation

HRID 658372 reaction equation
CN(C)CC[C:5]([NH:7][NH:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#[N:49].[CH3:52][C:53]([N:55]([CH3:57])[CH3:56])=O>>[F:24][C:18]1[CH:19]=[C:20]([I:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[C:9]1[O:25][C:5]([NH:49][CH2:52][CH2:53][N:55]([CH3:57])[CH3:56])=[N:7][N:8]=1

Participants

5

Reactant 4

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 31374DimethylacetamideHCID 68826032HCID 68826032, compound

Product 1

HCID 59026804HCID 59026804, compound

Conditions

Temperature
100 °C

Procedure

3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid N′-(3-dimethylamino-propionyl)-hydrazide (130 mg, 0.27 mmol) was dissolved in DMA (2 mL), and then PS-Triphenyl-phosphane (420 mg, 1.6 mmol, 6 eq), Trichloro-acetonitrile (77 mg, 0.53 mmol, 2 eq) and DIEPA (0.19 mL, 1.07 mmol, 4 eq) were added. The reaction mixture was stirred at 100° C. overnight, and then filtered. The filtrate was directly subjected to preparative HPLC to afford 32 mg of the desired product. LC/MS (Method A) [3.63 min; 467(M+1)]

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-8e3ab39305b44cd2862f541174afde8f
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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