Pyridine-2-sulfonyl chloride hydrochloride → 3-(3-{[(Pyridine-2-sulfonyl)-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2300455Notes

Reaction equation

HRID 2300455 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]([C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[CH:17][CH:16]=2)[CH:7]=1.Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35]>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]([S:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=2)(=[O:36])=[O:35])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[CH:17][CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 13791306Pyridine-2-sulfonyl chloride hydrochlorideHCID 542857593-{3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 545660013-(3-{[(Pyridine-2-sulfonyl)-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step A was prepared from 3-{3-[(4-thiazol-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, prepared in Step A of Example 11e, and pyridine-2-sulfonyl chloride hydrochloride, of Preparation 47, following the method described in Example 1, Step B using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 9.05 (s, 1H), 8.80 (d, 1H), 8.05 (m, 1H), 7.84 (m, 3H), 7.43 (m, 1H), 7.34 (d, 1H), 7.15 (m, 3H), 7.06 (d, 1H), 6.91 (d, 1H), 6.86 (s, 1H), 4.39 (s, 2H), 4.36 (s, 2H), 3.65 (s, 3H), 2.82 (t, 2H), 2.51 (t, 2H); MS 508 (M+1).

Sources & evidence

ORD record
ord-7c6e1b7c35bc4356852daff0e6732ae2
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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