4-But-2-ynyloxy-benzenesulfonyl chloride → HCID 22645020, compound

HRID 2084923Notes

Reaction equation

[F:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[O:8])=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[C:23]#[C:24][CH3:25]>>[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:12]2[CH2:13][CH2:14][N:9]([C:7]([NH:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)=[O:8])[CH2:10][CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:35])=[O:34])=[CH:29][CH:28]=1)[C:23]#[C:24][CH3:25]

Participants

Reactant 2

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

HCID 22645037HCID 22645037, compound

Product 1

HCID 22645020HCID 22645020, compoundYield 70%

Procedure

In the same manner as described in Step 2 of Example 215, ethyl 4-[(4-fluoroanilino)carbonyl]-2-piperazinecarboxylate (0.41 g, 1.4 mmol) and 4-but-2-ynyloxy-benzenesulfonyl chloride provided 0.49 g (70%) of ethyl 1-{[4-(2-butynyloxy)phenyl]sulfonyl}-4-[(4-fluoroanilino)carbonyl]-2-piperazinecarboxylate as a white powder. Electrospray Mass Spec 504.4 (M+H)+.

Sources & evidence

ORD record: ord-5718a53643b141df964f8bbb51c6dc52
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716833B2

Reaction notes

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