7-amino-3,4-dihydro-1H-quinolin-2-one → HCID 66711310, compound

HRID 1262157Notes

Reaction equation

HRID 1262157 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][CH:28]=1>>[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]([NH:26][C:27]3[CH:36]=[C:35]4[C:30]([CH2:31][CH2:32][C:33](=[O:37])[NH:34]4)=[CH:29][CH:28]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 52002427-amino-3,4-dihydro-1H-quinolin-2-oneHCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66711310HCID 66711310, compound

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-3,4-dihydro-1H-quinolin-2-one (0.043 g, 0.27 mmol) were reacted in an analogous manner to Example 908D at 50° C. for 16 h. Upon completion, the product was triturated and washed with acetone. LC/MS: 386 (M+H); HPLC: 2.920 minutes, 99% purity, MP: 310-313° C. 1H NMR (400 MHz, CDCl3 , 6, ppm): 8.56 (s, 1H), 7.97 (d, J=8.6 Hz, 1H), 7.65 (dd, J=7.8, 8.3 Hz, 1H), 7.47 (s, 1H), 7.23-7.16 (m, 3H), 7.07 (d, J=8.0 Hz, 1H), 7.02 (s, 1H), 6.96 (d, J=5.9 Hz, 1H), 3.88 (s, 3H), 2.93 (t, 2H), 2.64 (t, 2H).

Workup

  1. customUpon completion, the product was triturated
  2. washwashed with acetone
  3. custom2.920 minutes, 99% purity, MP: 310-313° C

Sources & evidence

ORD record
ord-50e13f6b6a9d4efe902de17a457c1458
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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