Benzenesulfonyl chloride → 3-(3-{[Benzenesulfonyl-(4-pyridin-3-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2117478Notes

Reaction equation

HRID 2117478 reaction equation
[CH3:1][O:2][C:3](=[O:27])[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]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH:7]=1.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:36])=[O:35])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 542431953-{3-[(4-Pyridin-3-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 539357793-(3-{[Benzenesulfonyl-(4-pyridin-3-yl-benzyl)-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-pyridin-3-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, of Step A, and benzenesulfonyl chloride following the method described in Example 1, Step B using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ8.79 (s, 1H), 8.58 (d, 1H), 7.87 (m, 3H), 7.61 (m, 1H), 7.54 (m, 2H), 7.40 (m, 3H), 7.18 (m, 3H), 7.03 (d, 1H), 6.88 (d, 1H), 6.79 (s, 1H), 4.36 (s, 2H), 4.33 (s, 2H), 3.65 (s, 3H), 2.79 (t, 2H), 2.48 (t, 2H); MS 501 (M+1).

Sources & evidence

ORD record
ord-b6d39c3f0148460db8d9bfd706ba964f
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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