7-Amino-6-fluoro-1,2,3,4-tetrahydroquinolin-2-one → 6-Fluoro-7-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3,4-dihydro-1H-quinolin-2-one

HRID 1262149Notes

Reaction equation

HRID 1262149 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]2)=[CH:11][CH:10]=1.[NH2:26][C:27]1[CH:36]=[C:35]2[C:30]([CH2:31][CH2:32][C:33](=[O:37])[NH:34]2)=[CH:29][C:28]=1[F:38]>>[F:38][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:27]=1[NH:26][C:15]1[N:14]=[CH:13][C:12]3=[CH:11][CH:10]=[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[N:17]3[N:16]=1)[NH:34][C:33](=[O:37])[CH2:32][CH2:31]2

Participants

3

Reactant 2

HCID 120408227-Amino-6-fluoro-1,2,3,4-tetrahydroquinolin-2-oneHCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 667119706-Fluoro-7-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3,4-dihydro-1H-quinolin-2-one

Procedure

Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.080 g, 0.21 mmol) and 7-Amino-6-fluoro-3,4-dihydro-1H-quinolin-2-one (0.045 g, 0.25 mmol) were reacted in an analogous manner to Example 908D at 50° C. for 16 h. The product was triturated and washed with acetone. LC/MS: 403.9 (M+H)HPLC: 2.966 min, 99% purity. MP: 300-305° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.57 (s, 1H), 7.91 (d, J=7.6 Hz, 1H) 7.62-7.53 (m, 2 h), 7.44 (s, 1H), 7.24-7.23 (m, 1H), 7.19-7.01 (m, 6H), 7.17-7.10 (m, 3H), 7.08 (s, 1H), 8.89 (s, 3H), 2.94 (t, 2H), 2.66, (t, 2H).

Workup

  1. customThe product was triturated
  2. washwashed with acetone
  3. custom2.966 min, 99% purity

Sources & evidence

ORD record
ord-9f0c9a84070a4fcfb88dbb51ce2a9e16
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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