1-methyl-1H-imidazole-4-sulfonyl chloride → 3-(3-{[(1-Methyl-1H-imidazole-4-sulfonyl)-(4-pyrazin-2-yl-benzyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2117527Notes

Reaction equation

HRID 2117527 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:26]=[N:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH:7]=1.[CH3:28][N:29]1[CH:33]=[C:32]([S:34](Cl)(=[O:36])=[O:35])[N: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:34]([C:32]2[N:31]=[CH:30][N:29]([CH3:28])[CH:33]=2)(=[O:36])=[O:35])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 541142043-{3-[(4-Pyrazin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 539955743-(3-{[(1-Methyl-1H-imidazole-4-sulfonyl)-(4-pyrazin-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 1from 3-{3-[(4-pyrazin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, of Step A of Example 11a, and 1-methyl-1H-imidazole-4-sulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 8.99 (d, 1H), 8.63 (m, 1H), 8.50 (d, 1H), 7.88 (d, 2H), 7.55 (s, 1H), 7.42 (s, 1H), 7.32 (d, 2H), 7.13 (m, 1H), 7.04-6.97 (m, 3H), 4.47 (s, 2H), 4.41 (s, 2H), 3.75 (s, 3H), 3.65 (s, 3H), 2.82 (t, 2H), 2.51 (t, 2H); MS 506 (M+1).

Sources & evidence

ORD record
ord-577dafcc058042d997179e8fabbd86b9
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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