Pyridine-3-sulfonyl chloride hydrochloride → 3-(3-{[(4-Pyrazol-1-yl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2117501Notes

Reaction equation

HRID 2117501 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)=[CH:17][CH:16]=2)[CH:7]=1.Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:29]=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)=[CH:17][CH:16]=2)[S:34]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)(=[O:36])=[O:35])[CH:7]=1

Participants

4

Reactant 2

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 540597813-{3-[(4-Pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 543859863-(3-{[(4-Pyrazol-1-yl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step B was prepared from 3-{3-[(4-pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, of Step A, and pyridine-3-sulfonyl chloride hydrochloride, of Preparation 2, following the method described in Example 1, Step B using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 9.03 (s, 1H), 8.77 (d, 1H), 8.04 (m, 1H), 7.87 (d, 1H), 7.68 (d, 1H), 7.54 (m, 2H), 7.42 (m, 1H), 7.14 (m, 3H), 7.07 (m, 1H), 6.88 (d, 1H), 6.83 (s, 1H), 6.44 (dd, 1H), 4.36 (s, 2H), 4.32 (s, 2H), 3.62 (s, 3H), 2.79 (t, 2H), 2.49 (t, 2H); MS 491 (M+1).

Sources & evidence

ORD record
ord-63d21e45d82e4b10a15db11fd5356ff9
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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