Acrylonitrile → HCID 22390516, compound

HRID 1072080Notes

Reaction equation

HRID 1072080 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[NH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][N:16]3[C:21]=2[C:20]([NH:22][C:23]2[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[N:27]=[CH:26]4)=[N:19][CH:18]=[N:17]3)[CH2:8][CH2:7]1>CO>[F:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][N:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:20]3[C:21]4=[C:13]([CH2:12][N:9]5[CH2:8][CH2:7][CH:6]([NH:5][CH2:3][CH2:2][C:1]#[N:4])[CH2:11][CH2:10]5)[CH:14]=[CH:15][N:16]4[N:17]=[CH:18][N:19]=3)=[CH:31][CH:30]=2)[CH:26]=[N:27]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 10151881HCID 10151881, compound

Product 1

HCID 22390516HCID 22390516, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acrylonitrile (0.2 mL, 30 equiv.) was added to a solution of [5-(4-amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (47 mg, 0.1 mmole) in MeOH (3 mL) at RT. Removal the solvent followed by radial chromatography (1 mm silica gel plate, gradient elution with DCM containing 0 to 2% MeOH) afforded 40 mg (76%) of the title compound as a solid. MS: 524 (M+H)+; HPLC Ret Time: 0.99 min (Xterra 3.0×50 mm S7 C18 column, 2 min gradient, 5 mL/min).

Workup

  1. customRemoval the solvent
  2. washfollowed by radial chromatography (1 mm silica gel plate, gradient elution with DCM containing 0 to 2% MeOH)

Sources & evidence

ORD record
ord-af623949870e4bb481b8e868908b1c89
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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