Methylamine → HCID 16059137, compound

HRID 1989076Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3-Dimethylcarbamoyl-phenylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (5.2 mg, 0.010 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 2.1 mg of 2-(3-dimethylcarbamoyl-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): 9.56 (br. S, 1H), 9.33 (s, 1H), 8.77 (s, 1H), 7.51 (dd, 1H, J=2.3 Hz, J=9.31 Hz), 7.34 (d, 1H, J=7.9 Hz), 7.11 (dd, 1H, J=1.7 Hz, J=7.8 Hz), 6.99 (br. S, 1H), 2.86-3.05 (m, 13H), 2.12-2.19 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C27H26N6O3: 482.21, Found: 483.2 (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-6a983f4f075e43aa8d0925b52cc5a74a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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