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

HRID 1989073Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3-Dimethylaminomethyl-phenylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (15 mg, 0.032 mmol) was dissolved in MeOH (1 mL) and methylamine (1 mL of 1.0 M solution in THF, 1.0 mmol) was added and the reaction mixture was heated at 80° C. After 16 h, the solution was cooled to rt and purified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min) and lyophilized to provide 2.3 mg of 2-(3-dimethylaminomethyl-phenylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide. 1H NMR (TFA salt) (400 MHz, CDCl3) δ (ppm): 9.51 (s, 1H), 9.35 (s, 1H), 8.75 (s, 1H), 7.01-7.50 (m, 7H), 3.90 (br s, 2H), 2.90-3.02 (m, 7H), 2.60 (s, 6H), 2.11-2.19 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C27H28N6O2: 468.23, Found: 469.1 (M+H).

Workup

temperaturethe solution was cooled to rt
custompurified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min)

Sources & evidence

ORD record: ord-bbfddda58e3c4423b7c65b6bb11f00d8
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

Loading…