Hydrochloric Acid → HCID 90312974, compound

HRID 1523750Notes

Reaction equation

HRID 1523750 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:3]=[CH:2]1.Cl.CCN([CH:19]([CH3:21])[CH3:20])C(C)C.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30]>C(#N)C>[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([N:9]1[CH2:10][CH2:11][CH:6]([C:4]2[N:3]=[CH:2][N:1]([S:29]([C:20]3[CH:19]=[CH:21][CH:25]=[CH:24][C:23]=3[Br:22])(=[O:31])=[O:30])[CH:5]=2)[CH2:7][CH2:8]1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 1784208734-(1H-imidazol-4-yl)piperidine

Product 1

HCID 90312974HCID 90312974, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 mL vial were added a stirbar, 4-(1H-imidazol-4-yl)piperidine.HCl (696 mg, 3.71 mmol), ACN (5 mL), and DIPEA (2.0 mL, 12 mmol). The mixture was then treated with 2-bromobenzene-1-sulfonyl chloride (900 mg, 3.52 mmol) and the mixture was stirred for 15.5 hours before concentrating to dryness and subjecting the residue to FCC to give the title compound (950 mg, 92%). MS (ESI): mass calcd. for C20H19Br2N3O4S2 586.92 m/z found 587.9 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.20 (dd, J=7.9, 1.8, 1H), 8.08 (dd, J=7.8, 1.7, 1H), 8.06 (d, J=1.3, 1H), 7.75 (dd, J=7.7, 1.3, 1H), 7.72 (dd, J=7.9, 1.2, 1H), 7.58-7.53 (m, 1H), 7.53-7.49 (m, 1H), 7.45-7.40 (m, 1H), 7.39-7.34 (m, 1H), 6.93-6.91 (m, 1H), 3.90-3.82 (m, 2H), 2.93-2.83 (m, 2H), 2.68-2.59 (m, 1H), 2.02 (dd, J=13.9, 3.0, 2H), 1.70-1.59 (m, 2H).

Workup

  1. concentrationbefore concentrating to dryness

Sources & evidence

ORD record
ord-0775ebb86531424088d84b18bc02763f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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