2-(5-Amino-1,3-dihydro-2H-isoindol-2-yl)acetamide → 2-{5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-isoindol-2-yl}-acetamide

HRID 1262151Notes

Reaction equation

HRID 1262151 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[CH2:32][N:31]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:30]2>COC(O)CC>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:26][C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[CH2:32][N:31]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:30]5)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 574160552-(5-Amino-1,3-dihydro-2H-isoindol-2-yl)acetamideHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 667123582-{5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-isoindol-2-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 3032390Propylene glycol methyl etherSolvent

Procedure

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.112 g, 0.298 mmol) and 2-(5-Amino-1,3-dihydro-isoindol-2-yl)-acetamide (0.077 g, 0.40 mmol) were reacted in an analogous manner to Example 908D at 50° C. for 16 h in methoxypropanol. Yellow solid precipitated out which was filtered off and washed with water (47 mg, 38%). Found to be pure desired product. LCMS=415.9 (M+H), HPLC rt=2.039 min, purity=96%. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.51 (s, 1H), 9.02 (s, 1H), 8.98 (s, 1H), 8.42 (dd, J=8.7 Hz, 2.3 Hz, 1H), 7.89 (s, 1H), 7.37 (d, J=8.6 Hz, 1H), 7.34 (s, 1H), 7.18-7.10 (m, 3H), 6.99-6.95 (m, 2H), 4.01 (s, 2H), 3.94 (s, 5H), 3.29 (s, 2H).

Workup

  1. customYellow solid precipitated out which
  2. filtrationwas filtered off
  3. washwashed with water (47 mg, 38%)
  4. customLCMS=415.9 (M+H), HPLC rt=2.039 min, purity=96%

Sources & evidence

ORD record
ord-3501e82f4cb649d4885e11a1b7e1f5a6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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