N,N-dimethyl-p-phenylenediamine → HCID 16059274, compound

HRID 1989007Notes

Reaction equation

HRID 1989007 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14]([C:16]1[C:17](=[O:39])[C:18]2[CH:23]=[N:22][C:21](S(C)(=O)=O)=[N:20][C:19]=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:15])[CH3:12]>>[CH2:11]([O:13][C:14]([C:16]1[C:17](=[O:39])[C:18]2[CH:23]=[N:22][C:21]([NH:7][C:6]3[CH:8]=[CH:9][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][CH:5]=3)=[N:20][C:19]=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:15])[CH3:12]

Participants

3

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 16059274HCID 16059274, compoundYield 46.7%

Procedure

Using the procedure outlined in Example 1(g) the title compound was prepared from 4-dimethylaminoaniline (5 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(e) above, 15 mg, 0.036 mmol). 7.9 mg of 2-(4-dimethylamino-phenylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester was obtained as a yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.31 (br, 1H), 8.53 (s, 1H), 7.82 (d, 1H), 7.61 (br, 1H), 7.41 (d, 1H), 7.29 (s, 1H), 7.17 (d, 1H), 6.76 (d, 1H), 6.46 (br, 2H), 4.39 (q, 2H), 3.03 (m, 4H), 2.89 (s, 6H), 2.22 (m, 2H), 1.37 (t, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C27H27N5O3: 470.21 (M+H), Found: 470.4.

Sources & evidence

ORD record
ord-3fb88611da114c10ab84ef3f112e3d8d
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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