Methanol → HCID 118294196, compound

HRID 2205183Notes

Reaction equation

HRID 2205183 reaction equation
B(Cl)(Cl)Cl.[NH2:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]([C@H:13]2[C@H:17]([OH:18])[C@H:16]([O:19]CC3C=CC=CC=3)[C@:15]([CH2:30][O:31]CC3C=CC=CC=3)([CH:27]([F:29])[F:28])[O:14]2)[C:8](=[O:39])[N:7]=1.N1C=CC=CC=1.CO>ClCCl>[NH2:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]([C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:19])[C@@:15]([CH:27]([F:28])[F:29])([CH2:30][OH:31])[O:14]2)[C:8](=[O:39])[N:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 25135Boron TrichlorideHCID 118294355HCID 118294355, compound

Product 1

HCID 118294196HCID 118294196, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BCl3 (2.46 mL, 2.46 mmol) was added to a cooled (−78° C.) solution of compound 30 (0.125 g, 0.246 mmol) in dry dichloromethane (10 mL). The mixture was cooled to 0° C. and pyridine (0.5 mL) and MeOH (2 mL) were added. The reaction mixture was evaporated to dryness under reduced pressure. Purification by prep-HPLC provided 31 (0.035 g, 44%) as a white solid. LC-MS (M+H)+=328.1

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-1358aac87a0d4fdebbeecdbf981e10f6
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

Loading…