Diisopropylethylamine → HCID 67155578, compound

HRID 389676Notes

Reaction equation

HRID 389676 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[C:20]=2[O:31][CH3:32])(=[O:18])=[O:17])[C:12](O)=[O:13])=[O:8])=[CH:4][CH:3]=1.[CH:33]1([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[ClH:1].[CH:33]1([N:36]2[CH2:41][CH2:40][N:39]([C:12](=[O:13])[C@@H:11]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:20]=3[O:31][CH3:32])(=[O:17])=[O:18])[CH2:10][NH:9][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:8])[CH2:38][CH2:37]2)[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47420041-CyclopropylpiperazineHCID 67155454HCID 67155454, compound

Product 1

HCID 67155578HCID 67155578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 82 (170 mg, 0.34 mmol) was dissolved in 10 ml DCM and N-cyclopropyl piperazine (134 mg, 0.38 mmol) was added followed by DIPEA (0.27 ml, 1.54 mmol) and TBTU (121 mg, 0.38 mmol). After 16 h stirring at RT, the solution was evaporated to dryness and purified by silica gel chromatography (Elution with DCM/methanol from 0 to 10% of methanol). The solid obtained after evaporation of the solvents was dissolved in DCM, HCl 2M in Et2O (5 ml) was added and the solvents were evaporated yielding a white powder. Yield: 112 mg, 50% MS (ES+): m/e=604.

Workup

  1. customthe solution was evaporated to dryness
  2. custompurified by silica gel chromatography (Elution with DCM/methanol from 0 to 10% of methanol)
  3. customThe solid obtained
  4. customafter evaporation of the solvents
  5. dissolutionwas dissolved in DCM
  6. additionHCl 2M in Et2O (5 ml) was added
  7. customthe solvents were evaporated
  8. customyielding a white powder

Sources & evidence

ORD record
ord-82958fc723944617a3f7157c07ab9e91
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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