8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester → HCID 68677276, compound

HRID 1989064Notes

Reaction equation

HRID 1989064 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[C:8]2[CH:13]=[N:12][C:11](S(C)(=O)=O)=[N:10][C:9]=2[N:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][CH2:24][CH2:23]3)[CH:19]=1)=[O:5])[CH3:2].OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[NH2:44][C:45]1[CH:50]=[CH:49][C:48]([CH:51]2[CH2:56][CH2:55][N:54]([C:57](=[O:62])[CH2:58][N:59]([CH3:61])[CH3:60])[CH2:53][CH2:52]2)=[CH:47][CH:46]=1>CC(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[C:8]2[CH:13]=[N:12][C:11]([NH:44][C:45]3[CH:50]=[CH:49][C:48]([CH:51]4[CH2:52][CH2:53][N:54]([C:57](=[O:62])[CH2:58][N:59]([CH3:60])[CH3:61])[CH2:55][CH2:56]4)=[CH:47][CH:46]=3)=[N:10][C:9]=2[N:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][CH2:24][CH2:23]3)[CH:19]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl esterHCID 131727836HCID 131727836, compound

Product 1

HCID 68677276HCID 68677276, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (20.5 mg, 0.050 mmol) and 1-[4-(4-amino-phenyl)-piperidin-1-yl]-2-dimethylamino-ethanone di-TFA salt (24 mg g, 0.050 mmol) were combined in i-PrOH (1 mL) and TEA (10.6 mg, 0.11 mmol) was added and the mixture was heated to 90° C. After 3 h, the reaction mixture was concentrated and purified by preparative HPLC (30 mL/min 5-100% MeCN/1120 gradient over 10 min) and lyophilized to provide 24 mg (80%) of 2-{4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenylamino}-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H NMR (300 MHz, CDCl3) δ (ppm): 9.31 (s, 1H), 9.10 (br s, 1H), 8.48 (s, 1H), 7.51 (d, 2H, J=8.1 Hz), 7.22-7.34 (2H), 7.13-7.16 (m 3H), 4.38 (q, 2H, J=7.0 Hz), 3.09 (br s, 2H), 2.95-3.02 (m, 6H), 2.71-2.80 (m, 2H), 2.39 (s, 6H), 2.11-2.22 (m, 2H), 1.55-1.93 (m, 4H), 1.39 (t, 3H, J=7.2 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by preparative HPLC (30 mL/min 5-100% MeCN/1120 gradient over 10 min)

Sources & evidence

ORD record
ord-80730d03c3ea4fac8f77b585f0f0274e
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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