Diisopropylethylamine → HCID 67155241, compound

HRID 389674Notes

Reaction equation

HRID 389674 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:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:20]=2[CH3:31])(=[O:18])=[O:17])[C:12]([OH:14])=O)=[O:8])=[CH:4][CH:3]=1.[CH:32]1([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][CH2:33]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].[ClH:1].[CH:32]1([N:35]2[CH2:40][CH2:39][N:38]([C:12](=[O:14])[C@@H:11]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:20]=3[CH3:31])(=[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])[CH2:37][CH2:36]2)[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47420041-CyclopropylpiperazineHCID 67155382HCID 67155382, compound

Product 1

HCID 67155241HCID 67155241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 78 (202 mg, 0.42 mmol) was dissolved in 10 ml DCM and N-cyclopropyl piperazine (105 mg, 0.84 mmol) was added followed by DIPEA (0.29 ml, 1.68 mmol) and TBTU (202 mg, 0.63 mmol). After stirring for 1 h 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. Yield: 163 mg, 59%. MS (ES+): m/e=588.

Workup

  1. customwas 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

Sources & evidence

ORD record
ord-c8fc62440a864aa6b43ed5290a3085dd
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

Loading…