Trifluoroacetate → HCID 11562717, compound

HRID 1714001Notes

Reaction equation

HRID 1714001 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:36](O)=[O:37])=[CH:19][C:20]=3[N:21]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][C:24]4[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CCN=C=NCCCN(C)C.Cl.[CH3:51][N:52]([CH3:57])[S:53]([NH2:56])(=[O:55])=[O:54]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:36]([NH:56][S:53]([N:52]([CH3:57])[CH3:51])(=[O:55])=[O:54])=[O:37])=[CH:19][C:20]=3[N:21]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][C:24]4[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:23]=4[C:22]=23)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 84468TrifluoroacetateHCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42640442HCID 42640442, compound

Product 1

HCID 11562717HCID 11562717, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.5 eq of DMAP was added to the trifluoroacetate salt of 14-cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acid (from Example 4) in dry DCM (0.1 M). Then 1.5 eq of EDAC.HCl was added and after 5 min of stirring at RT 1.5 eq of N,N-dimethylsulfamide. The reaction mixture was stirred overnight at RT. The solvent was removed in vacuo and the residue directly purified by RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (38%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue directly purified by RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-83d496991436491e9b0fc20f46e8fa48
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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