N-Methyl-D-glucamine → 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(cyclopropylmethyl)amino]-2-fluorobenzoic acid N-methyl-D-glucamine

HRID 551964Notes

Reaction equation

HRID 551964 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][N:18]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[C:19]3[CH:20]=[CH:21][C:22]([F:28])=[C:23]([CH:27]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:35][NH:36][CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39]>>[CH3:35][NH:36][CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][N:18]([CH2:29][CH:30]3[CH2:31][CH2:32]3)[C:19]3[CH:20]=[CH:21][C:22]([F:28])=[C:23]([CH:27]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 8567N-Methyl-D-glucamineHCID 117143995-[{4-[(4-Butylphenyl)ethynyl]benzyl}(cyclopropylmethyl)amino]-2-fluorobenzoic acid

Product 1

HCID 117143985-[{4-[(4-butylphenyl)ethynyl]benzyl}(cyclopropylmethyl)amino]-2-fluorobenzoic acid N-methyl-D-glucamine

Procedure

The title compound was prepared following procedure described in example 24 from 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(cyclopropylmethyl)amino]-2-fluorobenzoic acid (200 mg; 0.44 mmol) and N-methyl-D-glucamine (86 mg; 0.44 mmol) and obtained quantitatively as a brown powder. HPLC, Rt: 5.35 min purity: 98.7%), LC/MS, M−(ESI): 454.1. Analysis calculated for C30H30NO2F—C7H17−NO5-0.5 CH2Cl2-3.0 H20: calculated C, 60.27%, H, 7.28%, N, 3.75%; Found: C, 60.50%, H, 6.96%, N, 3.92%.

Workup

  1. customobtained quantitatively as a brown powder

Sources & evidence

ORD record
ord-6411da389069488fb0a4dfa6d96652d3
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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