Ethylamine → HCID 16059340, compound

HRID 1989011Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7](=[O:39])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:28]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[CH2:35][CH2:34][CH2:33]3)[CH:29]=1)=O)C.[CH2:40]([NH2:42])[CH3:41]>CO>[CH2:40]([NH:42][C:4]([C:6]1[C:7](=[O:39])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:28]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[CH2:35][CH2:34][CH2:33]3)[CH:29]=1)=[O:3])[CH3:41]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 8-indan-5-yl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester Cpd 1 (Example 1(g), 5 mg) in 1 mL of methanol was added 1 mL of ethylamine (2 M in methanol). The solution was stirred at 70° C. for 30 minutes. The solvent was evaporated and the product was purified by preparative HPLC as the formic acid salt (1 mg, yellow solid). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.71 (m, 1H), 9.35 (s, 1H), 8.83 (s, 1H), 8.24 (br, 1H), 7.69 (br, 1H), 7.42 (d, 1H), 7.27 (m, 3H), 7.17 (d, 1H), 6.67 (br, 2H), 3.50 (m, 2H), 3.25 (m, 4H), 3.03 (m, 4H), 2.92 (m, 4H), 2.55 (s, 3H), 2.22 (m, 2H), 1.27 (t, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C30H33N7O2: 524.27 (M+H), Found: 524.3.

Workup

customThe solvent was evaporated
customthe product was purified by preparative HPLC as the formic acid salt (1 mg, yellow solid)

Sources & evidence

ORD record: ord-1c16697fedcb4e139cfe0181a7a0b8f6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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