4-Bromobenzyl bromide → HCID 10005738, compound

HRID 549303Notes

Reaction equation

HRID 549303 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([S:11]([O-:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Li+].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(OC([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=O)(C)(C)C>>[ClH:1].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:11]([C:9]2[S:10][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[C:7]=3[CH:8]=2)(=[O:13])=[O:12])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 685274-Bromobenzyl bromideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

Product 1

HCID 10005738HCID 10005738, compound

Procedure

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.42 mmol) was treated with 4-bromobenzylbromide (0.59 mmol) as described in Method P above and then reacted further with tert-butyl-piperazine-1-carboxylate as described in Method Q. The BOC protecting group was removed using Method R. Yield 0.024 g (12% over three steps). White solid. 1H NMR (300 MHz, DMSO-d6) δ 8.99 (s, 1H), 8.18 (d, J=5.5 Hz, 1H), 8.02 (s, 1H), 7.69 (d, J=5.5 Hz, 1H), 7.53 (d, J=8.5 Hz, 2H), 7.17 (d, J=8.5 Hz, 2H), 4.95 (s, 2H), 3.62-3.68 (m, 4H), 3.27-3.32 (m, 4H); MS (ESI+) for C18H18BrN3O2S2. C1 H m/z 454 (M+H)+. HPLC 90%, RT 1.24 min (YMC ODS AQ, 33×3 mm, 20-50% acetonitrile in 1.5 min).

Workup

  1. customThe BOC protecting group was removed
  2. customHPLC 90%, RT 1.24 min (YMC ODS AQ, 33×3 mm, 20-50% acetonitrile in 1.5 min)

Sources & evidence

ORD record
ord-36f6601876504c6fbf88f4ae4617c639
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

Loading…