Methanol → HCID 59026665, compound

HRID 606083Notes

Reaction equation

HRID 606083 reaction equation
C([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:21]=2)[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)C.B(Br)(Br)Br.CO>ClCCl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][OH:3])[N:6]([CH2:19][C:20]3[O:24][N:23]=[C:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH:21]=3)[C:7]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 59026695HCID 59026695, compound

Product 1

HCID 59026665HCID 59026665, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (0.40 g, 0.96 mmol) in dichloromethane (25 mL) was cooled on an ice bath, and boron tribromide (2.4 mL of a 1 M solution in dichloromethane) was added. The reaction was stirred for 17 hours, and an analysis by HPLC indicated the presence of starting material. Additional boron tribromide (1 mL) was added after 17 hours and then again after 32 hours of reaction time. After 32 hours of reaction time, methanol was added, and the solvents were removed under reduced pressure. The residue was triturated with water, isolated by filtration, washed with diethyl ether, recrystallized from methanol, and dried under high vacuum at 100° C. to provide 0.14 g of (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl)methanol as a white solid, mp 247.0-248.0° C.

Workup

  1. customagain after 32 hours of reaction time
  2. additionwas added
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated with water
  5. customisolated by filtration
  6. washwashed with diethyl ether
  7. customrecrystallized from methanol
  8. customdried under high vacuum at 100° C.

Sources & evidence

ORD record
ord-ab1620f9b8544decb0417f30102fabce
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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