Aniline → {4-[(2-Phenyl-pyrimidine-5-carbonyl)-amino]-butyl)-phosphonic acid diethyl ester

HRID 219678Notes

Reaction equation

HRID 219678 reaction equation
F[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=CC=1.[CH2:24]([O:26][PH:27](=[O:31])[O:28][CH2:29][CH3:30])[CH3:25]>>[CH2:24]([O:26][P:27]([CH2:21][CH2:22][CH2:23][CH2:18][NH:17][C:14]([C:11]1[CH:12]=[N:13][C:8]([C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)=[N:9][CH:10]=1)=[O:16])(=[O:31])[O:28][CH2:29][CH3:30])[CH3:25]

Participants

4

Reactant 3

HCID 6115AnilineHCID 450733632-(3-Fluorophenyl)pyrimidine-5-carboxylic acidHCID 178476833HCID 178476833, compound

Product 1

HCID 16666096{4-[(2-Phenyl-pyrimidine-5-carbonyl)-amino]-butyl)-phosphonic acid diethyl ester

Procedure

Following procedures similar to those of Example 5 but substituting 2-phenyl-pyrimidine-5-carboxylic acid for 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid, and substituting (4-aminobutyl)-phosphonic acid diethyl ester oxalate for aniline, there is prepared 14-[(2-phenyl-pyrimidine-5-carbonyl)-amino]-butyl)-phosphonic acid diethyl ester as a solid. MS: 392 (M+H); 1H NMR (300 MHz, CDCl3): δ 1.31 (t, 6H), 1.77 (m, 6H), 3.48 (q, 2H), 3.97-4.19 (m, 4H), 7.40-7.58 (m, 3H), 7.84 (bs, N—H), 8.40-8.57 (m, 2H), 9.23 (s, 2H); IC50=23.5 nM.

Sources & evidence

ORD record
ord-614f82828dab44bdbc9b5039d45f3e6f
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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