3-Amino-N,N-dimethylbenzamide → HCID 68677539, compound

HRID 1989075Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (20 mg, 0.048 mmol) and 3-amino-N,N-dimethyl-benzamide (8 mg, 0.05 mmol) were combined in i-PrOH (2 mL) and heated to 90° C. After 15 h, the reaction mixture was concentrated and purified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min) and lyophilized to provide 15.6 mg of 2-(3-dimethylcarbamoyl-phenylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.31 (s, 1H), 1.13 (s, 1H), 7.46 (br s, 1H), 7.33 (d, 1H, J=7.9 Hz), 7.16-7.21 (m, 2H), 7.10 (d, 1H, J=7.6 Hz), 6.96 (br s, 2H), 4.29 (q, 2H, J=7.1 Hz), 2.97-3.04 (m, 5H), 2.85-2.93 (m, 5H), 2.14 (p, 2H, J=7.4 Hz), 1.29 (t, 3H, J=7.1 Hz)

Workup

concentrationthe reaction mixture was concentrated
custompurified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min)

Sources & evidence

ORD record: ord-79602ff0d0964ae7a7736923381f5efc
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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