Hydrochloric Acid → HCID 53378226, compound

HRID 1504750Notes

Reaction equation

HRID 1504750 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]([CH3:33])[CH2:6][CH2:7][NH:8][C:9](=[O:32])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:12]=1[CH3:31].CN(C(ON1N=N[C:44]2[CH:45]=[CH:46][CH:47]=N[C:43]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:58][C:59](N(C)C)=[O:60]>CC#N.CCOC(C)=O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([N:13]2[C:14]3[C:19](=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:11]([CH2:10][C:9]([NH:8][CH2:7][CH2:6][N:5]([CH3:33])[CH2:4][CH2:3][NH:2][C:59](=[O:60])[CH2:58][CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:43]\[CH2:44]/[CH:45]=[CH:46]\[CH2:47]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:31]\[CH2:47]/[CH:46]=[CH:45]\[CH2:44][CH3:43])=[O:32])=[C:12]2[CH3:31])=[O:30])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67426942HCID 67426942, compound

Product 1

HCID 53378226HCID 53378226, compoundYield 219.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

This HCl salt of N-(2-((2-aminoethyl)(methyl)amino)ethyl)-2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamide (0.38 mmol) was taken up in 5 mL of CH3CN along with DHA (210 mg, 0.64 mmol), HATU (267 mg, 0.67 mmol) and DMA (334 μL, 2.01 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and diluted with EtOAc (25 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (95% CH2Cl2, 5% MeOH) afforded 320 mg of (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-((2-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamido)ethyl)(methyl)amino)ethyl)docosa-4,7,10,13,16,19-hexaenamide (65% yield). MS (EI) calcd for C46H59ClN4O4: 766.42; found 767 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (95% CH2Cl2, 5% MeOH)

Sources & evidence

ORD record
ord-4fbdab1b1bc041ffa4f03eb206f2c498
Source dataset
uspto-grants-2015_12
Patent number
US09216224B2

Reaction notes

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