Diisopropylethylamine → HCID 178527589, compound

HRID 1523748Notes

Reaction equation

HRID 1523748 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26]>CN(C=O)C>[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 178511715HCID 178511715, compound

Product 1

HCID 178527589HCID 178527589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 20 mL vial were added a stir-bar, trans-4-aminocyclohexanol (683 mg, 4.50 mmol), DMF (5 mL), and DIPEA (2.0 mL, 12 mmol). The mixture was then treated with 2-bromobenzene-1-sulfonyl chloride (1.00 g, 3.93 mmol) and the mixture stirred for 2 hours before subjecting the vial's content to FCC to give the title compound. (978 mg, 74%). MS (ESI): mass calcd. for C12H16BrNO3S 333.00, m/z found 334.0 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.12 (dd, J=7.8, 1.7, 1H), 7.70 (dd, J=7.8, 1.2, 1H), 7.49-7.43 (m, 1H), 7.43-7.37 (m, 1H), 5.10 (d, J=7.5, 1H), 3.62-3.47 (m, 1H), 3.11-3.01 (m, 1H), 2.12 (s, 1H), 1.91-1.75 (m, 4H), 1.31-1.15 (m, 4H).

Workup

  1. additionTo a 20 mL vial were added a stir-bar

Sources & evidence

ORD record
ord-a5d4aa4927ce4fdb9dd588beb663e45c
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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