Methanol → HCID 66807330, compound

HRID 1844052Notes

Reaction equation

HRID 1844052 reaction equation
C(ON=O)CC(C)C.N[C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:26]=3[C:27]([F:30])([F:29])[F:28])[C:17]2=[O:20])=[CH:12][C:11]=1[F:31].CO.C(Cl)(Cl)(Cl)[Cl:35]>C(Cl)(Cl)Cl>[Cl:35][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:26]=3[C:27]([F:30])([F:29])[F:28])[C:17]2=[O:20])=[CH:12][C:11]=1[F:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 5943Carbon TetrachlorideHCID 8053Isoamyl NitriteHCID 66803632HCID 66803632, compound

Product 1

HCID 66807330HCID 66807330, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Isoamylnitrite (107.7 mg, 0.91 mmol) was added to the stirred solution of 7-amino-6-fluoro-2-(4-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (I-79b: 100 mg, 0.306 mmol) in CCl4 (10 mL). The resulting mixture was stirred for 1 hour at 70° C. The reaction was monitored by TLC (5% methanol in CHCl3). The reaction mixture was concentrated to yield the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), followed by preparative HPLC afforded 10 mg of the product (10% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto yield the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-e47a026da103413aa1c63e20d1336a2f
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…