2-Thiazolesulfonyl chloride → 3-(3-{[(4-Pyrazol-1-yl-benzyl)-(thiazole-2-sulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2117585Notes

Reaction equation

HRID 2117585 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.[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[S:32](Cl)(=[O:34])=[O:33]>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:32]([C:28]2[S:27][CH:31]=[CH:30][N:29]=2)(=[O:34])=[O:33])[CH:7]=1

Participants

4

Reactant 2

HCID 115792352-Thiazolesulfonyl chlorideHCID 540597813-{3-[(4-Pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 543934673-(3-{[(4-Pyrazol-1-yl-benzyl)-(thiazole-2-sulfonyl)-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 A of Example 1 from 3-{3-[(4-pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, prepared in Step A of Example 11 h, and thiazole-2-sulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 7.95 (d, 1H), 7.88 (d, 1H), 7.69 (d, 1H), 7.60 (d, 1H), 7.54 (d, 2H), 7.19-7.12 (m, 3H), 7.04 (m, 1H), 6.93 (m, 2H), 6.44 (m, 1H), 4.49 (s, 2H), 4.46 (s, 2H), 3.64 (s, 3H), 2.82 (t, 2H), 2.51 (t, 2H); MS 497 (M+1).

Sources & evidence

ORD record
ord-426d22b18c0d43ccbb3706b2976c102b
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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