Methanesulfonyl chloride → HCID 178439653, compound

HRID 1818522Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]2[NH:39][N:38]=[N:37][N:36]=2)[CH:30]=1)[C:8]1[CH:28]=[CH:27][C:11]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[C:16]([OH:23])[C:15]=2[CH2:24][CH2:25][CH3:26])=[CH:10][CH:9]=1>>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([CH:7]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]4[NH:39][N:38]=[N:37][N:36]=4)[CH:30]=3)[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:28][CH:27]=2)=[C:15]([CH2:24][CH2:25][CH3:26])[C:16]=1[OH:23])(=[O:22])[CH3:21]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 178439651HCID 178439651, compound

Product 1

HCID 178439653HCID 178439653, compound

Procedure

The title compound is prepared essentially as described in Example 74 employing methane sulfonyl chloride and 1-[4-(4-{amino-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone to give 22 mg, 28%, as a white solid. 1H NMR (DMSO-d6) δ 12.86 (s, 1H), 8.49 (d, 1H), 8.17 (s, 1H), 7.91-7.94 (m, 1H), 7.80 (d, 1H), 7.60-7.62 (m, 2H), 7.44-7.51 (m, 4H), 6.72 (d, 1H), 5.81 (d, 1H), 5.25 (s, 2H), 2.75 (s, 3H), 2.57-2.62 (m, 5H), 1.46-1.53 (m, 2H), 0.87 (t, 3H). LCMS M+1 536.

Workup

customto give 22 mg, 28%

Sources & evidence

ORD record: ord-0007adcf2faa428b96ece3b3c24e15b5
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598423B2

Reaction notes

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