4-Chlorobenzenesulfonyl chloride → 3-(3-{[(4-Chloro-benzenesulfonyl)-(4-pyrimidin-2-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2300473Notes

Reaction equation

HRID 2300473 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[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH:7]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=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:35]([C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 536352203-{3-[(4-Pyrimidin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 543528153-(3-{[(4-Chloro-benzenesulfonyl)-(4-pyrimidin-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 following the method described in Step B of Example 1 from 3-{3-[(4-pyrimidin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, prepared in Step A of Example 11z, and 4-chlorobenzensulfonyl chloride using triethylamine in place of N,N-iisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 8.78 (m, 2H), 8.28 (d, 2H), 7.76 (d, 2H), 7.46 (d, 2H), 7.15 (m, 4H), 7.03 (d, 1H), 6.88 (d, 1H), 6.80 (s, 1H), 4.36 (s, 2H), 4.29 (s, 2H), 3.63 (s, 3H), 2.79 (t, 2H), 2.48 (t, 2H); MS 536 (M+1).

Sources & evidence

ORD record
ord-df85eaf35a58443c9d30f16a31b04826
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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