HCID 16059271, compound → HCID 16059276, compound

HRID 1989009Notes

Reaction equation

HRID 1989009 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:5])C>O1CCCC1.[OH-].[Na+]>[CH2:35]1[C:36]2[C:32](=[CH:31][C:30]([N:28]3[C:9]4[N:10]=[C:11]([NH:14][C:15]5[CH:16]=[CH:17][C:18]([N:21]6[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]6)=[CH:19][CH:20]=5)[N:12]=[CH:13][C:8]=4[C:7](=[O:39])[C:6]([C:4]([OH:5])=[O:3])=[CH:29]3)=[CH:38][CH:37]=2)[CH2:33][CH2:34]1

Participants

4

Reactant 1

HCID 16059271HCID 16059271, compound

Product 1

HCID 16059276HCID 16059276, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydrolysis 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), 50 mg) in a mixture of tetrahydrofuran (THF) and 1 N sodium hydroxide solution at an elevated temperature gave 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 Cpd 6, which was purified using preparative HPLC, resulting in a formic acid salt form (28 mg, yellow solid). 1H NMR (300 MHz, CDCl3) δ (ppm): 9.38 (s, 1H), 8.80 (s, 1H), 8.35 (br, 1H), 7.83 (br, 1H), 7.42 (m, 2H), 7.20 (m, 4H), 6.65 (br, 2H), 3.20 (m, 4H), 3.03 (m, 4H), 2.88(m, 4H), 2.60(m, 4H), 2.50 (s, 3H), 2.20 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H28N6O3: 497.22 (M+H), Found: 497.5.

Sources & evidence

ORD record
ord-a0a685d005b34e0db8b6f05d09c6859a
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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