Water → HCID 22480085, compound

HRID 1272745Notes

Reaction equation

HRID 1272745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[N:10](COCCOC)[N:9]=2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O.N1C=CC=C[CH:35]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:35])=[O:31])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22479706HCID 22479706, compound

Product 1

HCID 22480085HCID 22480085, compoundYield 19%

Conditions

Temperature
80 °C

Procedure

To a solution of 1-{[3-(4-fluorophenyl)-5-amino(1H-indazolyl)]methoxy}-2-methoxyethane (100 mg, 0.32 mmol) in pyridine (3 mL) was added benzoyl chloride (45 μL, 0.38 mmol). The solution was stirred for 12 hours when water (80 mL) was added and the solid filtered. The solid was then taken up in methanol (3 mL) and 6N HCl (3 mL) and heated to 80° C. for 3 hours. Water (80 mL) was then added and the solid filtered and dried to give the title compound (20 mg, 19% yield). 1H NMR (DMSO-d6) δ 13.3 (br s, 1H), 10.37 (s, 1H), 8.57 (s, 1H), 8.0–7.9 (m, 5H), 7.78 (d, 1H), 7.6–7.5 (m, 4H), 7.40 (t, 2H); ES-MS (m/z) 332 [M+1]+.

Workup

  1. additionwas added
  2. filtrationthe solid filtered
  3. additionWater (80 mL) was then added
  4. filtrationthe solid filtered
  5. customdried

Sources & evidence

ORD record
ord-e90874af58df4d39b015ac6b9f58186b
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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