(S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → (S)-N-(2,3-Dihydroxypropoxy)-6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

HRID 641609Notes

Reaction equation

HRID 641609 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]=1[C:20](OC1C=CC=CC=1)=[O:21].CC1(C)[O:34][C@H:33]([CH2:35][O:36][NH2:37])[CH2:32][O:31]1>>[OH:34][C@@H:33]([CH2:32][OH:31])[CH2:35][O:36][NH:37][C:20]([C:11]1[C:12](=[O:19])[N:13]([CH3:18])[C:14](=[O:17])[N:15]([CH3:16])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:21]

Participants

3

Reactant 2

HCID 14814202(S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 25109024(S)-N-(2,3-Dihydroxypropoxy)-6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

Procedure

Example 37 was synthesized following a similar procedure described in the synthesis of Example 2 by treatment of compound 2A with (S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine (See, Bailey et al., J. Med. Chem., 34, 1991, 51-65), followed by acid hydrolysis of the resulting material. 1H NMR (400 MHz, CDCl3) δ 7.46 (m, 2 H) 6.79 (t, J=8.0 Hz, 1 H) 3.89 (m, 3 H) 3.66 (m, 1 H) 3.55 (m, 1 H) 3.31 (s, 3 H) 3.02 (s, 3 H). [M+H] calc'd for C16H18FIN4O6, 509; found, 509.

Workup

  1. customExample 37 was synthesized
  2. customfollowed by acid hydrolysis of the resulting material

Sources & evidence

ORD record
ord-217f8fa8729c47f9ba16f78e82f90b51
Source dataset
uspto-grants-2010_04
Patent number
US07696218B2

Reaction notes

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