Pyridine → HCID 21997630, compound

HRID 1977123Notes

Reaction equation

HRID 1977123 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[NH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[S:19][CH2:20][C:21]#[N:22]>C1COCC1>[C:21]([CH2:20][S:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[NH:11][C:1](=[O:3])[CH3:2])#[N:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 21997633HCID 21997633, compound

Product 1

HCID 21997630HCID 21997630, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (1.5 ml) in THF (10 ml) and subsequently pyridine (1.7 ml) in THF (10 ml) was added to a stirred solution of (2-amino-4-fluoro-phenylsulfanyl)acetonitrile (3.5 g) in THF (30 ml) at 0° C. The mixture was stirred at 0° C. for 50 min. Then the solvent was removed in vacuo and the residue was triturated with water (80 ml). The precipitate was filtered off and dried yielding 3.7 g (86%) of the title compound as yellow crystals; mp 113-115° C.; 1H-NMR (DMSO-d6), δ (ppm): 9.59 (s, 1H, NH), 7.73-7.57 (m, 2H, Ar—H), 7.19-7.05 (m, 1H, Ar—H), 4.05 (s, 2H, CH2), 2.12 (s, 3H, CH3). The title compound was used for the next step without further purification.

Workup

  1. customThen the solvent was removed in vacuo
  2. customthe residue was triturated with water (80 ml)
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-e3c4a82604cc411eab2355ef3c80a36e
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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