Hydrochloric Acid → HCID 178450409, compound

HRID 1262438Notes

Reaction equation

HRID 1262438 reaction equation
[OH-:1].[Na+].[C:3]([O:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](S(C)(=O)=O)=[N:22]3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].Cl>>[C:3]([O:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([OH:1])=[N:22]3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66712170HCID 66712170, compound

Product 1

HCID 178450409HCID 178450409, compoundYield 103%

Conditions

Temperature
80 °C

Procedure

5M NaOH (4 mL, 20 mmol) was added to 7-(3-tert-Butoxymethyl-phenyl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine (0.398 g, 1.11 mmol) and the reaction was stirred and heated at 80° C. for 2 hours. The reaction was let cool to room temperature and HCl (−2 mL) was then added dropwise to the reaction mixture to precipitate the product (pH 1), which was filtered immediately and washed with water and dried in vacuo to afford 7-(3-tert-Butoxymethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (340 mg, 100%) as a brown solid. 1H-NMR (DMSO-d6): 8.64 (s, 1H), 8.21 (d, 1H, J=7.59 Hz), 8.14 (s, 1H), 7.31 (t, 1H, J=7.59 Hz), 7.18 (d, 1H, J=7.59 Hz), 6.88 (s, 1H), 6.56 (s, 1H), 4.47 (s, 2H), 1.25 (s, 9H).

Workup

  1. temperatureThe reaction was let cool to room temperature
  2. customto precipitate the product (pH 1), which
  3. filtrationwas filtered immediately
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-31e4964133ee46caba07e667679d2946
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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