Methylamine → 2-[4-(3-Dimethylamino-2-hydroxy-propoxy)-phenylamino]-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide

HRID 1989012Notes

Reaction equation

C(O[C:4]([C:6]1[C:7](=[O:40])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:28])[CH2:24][N:25]([CH3:27])[CH3:26])=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH2:36][CH2:35][CH2:34]3)[CH:30]=1)=[O:5])C.[CH3:41][NH2:42]>CO>[CH3:41][NH:42][C:4]([C:6]1[C:7](=[O:40])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:28])[CH2:24][N:25]([CH3:26])[CH3:27])=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH2:36][CH2:35][CH2:34]3)[CH:30]=1)=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-[4-(3-dimethylamino-2-hydroxy-propoxy)-phenylamino]-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 2(c), 8 mg) in 1 mL of methanol was added 1 mL of methylamine (40 wt. % in water). The solution was stirred at 70° C. for 30 minutes. The solvent was evaporated to yield a yellow solid (6.6 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.64 (m, 1H), 9.35 (s, 1H), 8.82 (s, 1H), 7.39 (m, 2H), 7.27 (m, 1H), 7.15 (m, 2H), 6.66 (br, 2H), 4.06 (m, 1H), 3.93 (m, 2H), 3.02 (m, 5H), 2.89 (m, 4H), 2.56 (dd, 1H), 2.35 (m, 7H), 2.22 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H32N6O4: 529.25 (M+H), Found: 529.2.

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-11aec621935042c59e1e25205f74bcd9
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

Loading…