3-(Morpholin-4-ylmethyl)aniline → 8-Indan-5-yl-2-(3-morpholin-4-ylmethyl-phenylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

HRID 1989029Notes

Reaction equation

HRID 1989029 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:15]1[C:23]2[C:18](=[CH:19][C:20]([N:24]3[C:29]4[N:30]=[C:31](S(C)(=O)=O)[N:32]=[CH:33][C:28]=4[C:27](=[O:38])[C:26]([C:39]([NH2:41])=[O:40])=[CH:25]3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1>>[CH2:15]1[C:23]2[C:18](=[CH:19][C:20]([N:24]3[C:29]4[N:30]=[C:31]([NH:14][C:10]5[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:1]6[CH2:6][CH2:5][O:4][CH2:3][CH2:2]6)[CH:9]=5)[N:32]=[CH:33][C:28]=4[C:27](=[O:38])[C:26]([C:39]([NH2:41])=[O:40])=[CH:25]3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 10964063-(Morpholin-4-ylmethyl)anilineHCID 686788178-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

Product 1

HCID 160595328-Indan-5-yl-2-(3-morpholin-4-ylmethyl-phenylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amideYield 43.1%

Procedure

Using the procedure outlined in Example 23 (a and c), the title compound was prepared from 3-morpholin-4-ylmethyl-phenylamine (5 mg) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide (from Example 23 (b), 7 mg). Purification by preparative HPLC (32 mL/min, 5-100% H2O/MeCN (0.01% TFA, v/v) gradient over 10 min) gave the title compound as a white solid (3.9 mg, 35%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.55 (br, 1H), 9.42 (s, 1H), 8.83 (s, 1H), 7.60 (br, 1H), 7.50 (br, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.24 (s, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.13 (br, 2H), 6.23 (br, 1H), 4.00 (br, 4H), 3.32 (br, 2H), 3.08 (t, J=7.3 Hz, 2H), 3.00 (t, J=7.3 Hz, 2H), 2.72 (br, 2H), 2.23 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H28N6O3: 497.22 (M+H), Found: 497.1.

Workup

  1. customPurification by preparative HPLC (32 mL/min, 5-100% H2O/MeCN (0.01% TFA, v/v) gradient over 10 min)

Sources & evidence

ORD record
ord-807a4b04805947b59f38d5945ea1e269
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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