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

HRID 1262158Notes

Reaction equation

HRID 1262158 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: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:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[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 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 667123996-Fluoro-7-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3,4-dihydro-1H-quinolin-2-one

Procedure

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-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 were reacted in an analogous manner to Example 908D at 50° C. for 32 h. Upon completion, the product was triturated and washed with acetone. LC/MS: 404.9 (M+H); HPLC: 2.770 minutes, 99% purity. MP: 295° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.91 (s, 1H), 8.65 (s, 1H), 8.34 (d, J=9.9 Hz, 1H), 7.48-7.42 (m, 2H), 7.10-7.05 (m, 2H), 6.94-6.90 (m, 2H), 4.05 (s, 3H), 3.06 (t, 2H), 2.71 (t, 2H).

Workup

  1. customUpon completion, the product was triturated
  2. washwashed with acetone
  3. custom2.770 minutes, 99% purity

Sources & evidence

ORD record
ord-cfbfb1c0af4d43fb90307bc4a0bc58a9
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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