Triethylamine → HCID 58832263, compound

HRID 1989008Notes

Reaction equation

HRID 1989008 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:12])[C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8].[CH2:13]([O:15][C:16]([C:18]1[C:19](=[O:41])[C:20]2[CH:25]=[N:24][C:23](S(C)(=O)=O)=[N:22][C:21]=2[N:30]([C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[CH2:37][CH2:36][CH2:35]3)[CH:31]=1)=[O:17])[CH3:14].C(N(CC)CC)C>>[CH2:13]([O:15][C:16]([C:18]1[C:19](=[O:41])[C:20]2[CH:25]=[N:24][C:23]([NH:8][C:7]3[CH:9]=[CH:10][CH:11]=[C:5]([N:4]([CH3:12])[CH3:3])[CH:6]=3)=[N:22][C:21]=2[N:30]([C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[CH2:37][CH2:36][CH2:35]3)[CH:31]=1)=[O:17])[CH3:14]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 58832263HCID 58832263, compoundYield 39%

Procedure

Using the procedure outlined in Example 1(g) the title compound was prepared from 3-dimethylaminoaniline dihydrochloride (7.6 mg, 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) at the presence of triethylamine (11 μL, 0.072 mmol). 6.6 mg of 2-(3-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 (300 MHz, CDCl3) δ (ppm): 9.41 (br, 1H), 8.53 (s, 1H), 7.47 (br, 1H), 7.40 (d, 1H), 7.29 (s, 1H), 7.18 (d, 1H), 6.90 (m, 2H), 6.50 (m, 2H), 4.39 (q, 2H), 3.00 (m, 4H), 2.80 (s, 6H), 2.21 (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-ee3b82d8ed334d7b8852dd08a4f22d3b
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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