1-Cyclohexenylboronic acid → 2-Cyclohex-1-enyl-4-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenylamine

HRID 930145Notes

Reaction equation

HRID 930145 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][NH:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[NH2:16].[C:17]1(B(O)O)[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1>>[C:17]1([C:2]2[CH:7]=[C:6]([CH:8]3[CH2:13][NH:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]3)[CH:5]=[CH:4][C:3]=2[NH2:16])[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 597711772-Bromo-4-(1,1-dioxo-1lambda6[1,2,6]thiadiazinan-4-yl)-phenylamine

Product 1

HCID 597712852-Cyclohex-1-enyl-4-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenylamineYield 65%

Procedure

2-Bromo-4-(1,1-dioxo-1λ6-[1,2,6]thiadiazinan-4-yl)-phenylamine (as prepared in the previous step, 46.9 mg, 0.153 mmol) was reacted with cyclohexane-1-enyl boronic acid (24.1 mg, 0.191 mmol) according to the Suzuki coupling procedure of Example 4, step (e) and purified on silica (20-100% EtOAc-hexane) to afford the title compound (30.7 mg, 65%): Mass spectrum (ESI, m/z): Calcd. for C15H21N3O2S, 308.1 (M+H). found 308.1.

Workup

  1. custompurified on silica (20-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-9116dbee2c974dd4acf1834fe1f8a740
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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