2-Phthalimidoethanesulfonyl chloride → HCID 86636381, compound

HRID 542050Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].FC(F)(F)C(O)=O.[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:45]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH2:44].[O:46]=[C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49](=[O:56])[N:48]1[CH2:57][CH2:58][S:59](Cl)(=[O:61])=[O:60]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:45]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][S:59]([CH2:58][CH2:57][N:48]1[C:47](=[O:46])[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49]1=[O:56])(=[O:60])=[O:61]

Participants

Reactant 2

HCID 3087392-Phthalimidoethanesulfonyl chloride

HCID 86636148HCID 86636148, compound

Product 1

HCID 86636381HCID 86636381, compoundYield 20%

Procedure

The desired compound was prepared according to the procedure of Example D20, step A, using 6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine tris(trifluoroacetate) and 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonyl chloride as the starting materials in 20% yield. LCMS for C27H23ClN7O4S (M+H)+: m/z=575.9.

Sources & evidence

ORD record: ord-9003edfbc41c482999f0dfdd059cfc5a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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