Acetonitrile → HCID 66711931, compound

HRID 1262390Notes

Reaction equation

HRID 1262390 reaction equation
[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[N:6]2[N:5]=1)=[O:3].Br[CH2:21][C:22]([NH2:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].C(#N)C>>[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH2:21][C:22]([NH2:24])=[O:23])[N:6]2[N:5]=1)=[O:3]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 136360288HCID 136360288, compound

Product 1

HCID 66711931HCID 66711931, compoundYield 87.1%

Conditions

Temperature
60 °C

Procedure

2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (0.68 g, 2.5 mmol), 2-Bromoacetamide (0.414 g, 3.00 mmol), Potassium carbonate (0.7049 g, 5.100 mmol), and Acetonitrile (20 mL, 500 mmol) were combined in a round bottom flask and heated at 60° C. for 19 hours. The solid was filtered through Celite and washed with DCM. The filtrate was concentrated and purified via normal phase silica gel chromatography eluting with dichloromethane /methanol to yield a yellow solid, 2-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenoxy]-acetamide (719 mg, 87%). LCMS: m/z=331.16 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.31 (s, 1H), 7.75 (m, 1H), 7.50 (m, 2H), 7.36 (br s, 1H), 7.32 (d, 1H, J=4.7 Hz), 7.16 (m, 2H), 7.09 (d, 1H, J=8.4 Hz), 4.52 (s, 2H), 2.92 (s, 3H).

Workup

  1. filtrationThe solid was filtered through Celite
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified via normal phase silica gel chromatography
  5. washeluting with dichloromethane /methanol

Sources & evidence

ORD record
ord-d3e257147fbe4b0d8a215e721aee3e3e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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