Ethanesulfonyl chloride → HCID 69015059, compound

HRID 541627Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:47]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[CH2:48]([S:50](Cl)(=[O:52])=[O:51])[CH3:49]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:47]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][N:43]([S:50]([CH2:48][CH3:49])(=[O:52])=[O:51])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 86636141HCID 86636141, compound

Product 1

HCID 69015059HCID 69015059, compoundYield 41%

Procedure

The desired compound was prepared according to the procedure of Example A42, using N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-2-piperidin-4-ylacetamide bis(trifluoroacetate) and ethanesulfonyl chloride as starting materials in 41% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.40 (s, 1H), 9.36 (s, 1H), 9.28 (s, 1H), 8.12 (s, 1H), 7.98 (s, 1H), 7.73 (s, 1H), 7.21 (d, 1H), 7.04 (m, 2H), 6.87 (d, 1H), 6.78 (d, 1H), 3.60 (m, 2H), 3.01 (m, 2H), 2.83 (m, 6H), 2.27 (m, 2H), 1.91 (m, 1H), 1.78 (m, 2H), 1.22 (m, 2H), 1.20 (m, 3H). LCMS for C27H32ClN6O3S (M+H)+: m/z=555.2.

Sources & evidence

ORD record: ord-a88e7f5c0da349cda5bb72ba257d987c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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