Dimethylformamide → HCID 10053957, compound

HRID 2056955Notes

Reaction equation

HRID 2056955 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CC[N:15]([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])C.[CH3:22][N:23](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:24].F[P-](F)(F)(F)(F)F.[CH:46]1C=NC2N(O)N=NC=2C=1.[NH2:56][C:57]1[C:58]([O:72][CH3:73])=[C:59]([NH:67][S:68]([CH3:71])(=[O:70])=[O:69])[CH:60]=[C:61]([C:63]([CH3:66])([CH3:65])[CH3:64])[CH:62]=1.CN([CH:77]=[O:78])C>CCOC(C)=O>[C:63]([C:61]1[CH:60]=[C:59]([NH:67][S:68]([CH3:71])(=[O:70])=[O:69])[C:58]([O:72][CH3:73])=[C:57]([NH:56][C:10]([C:2]2[N:1]([CH3:46])[C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][C:8]=3[O:78][C:77]2[CH:18]=[CH:16][N:15]=[C:19]([CH2:20][N:23]([CH3:24])[CH3:22])[CH:21]=2)=[O:12])[CH:62]=1)([CH3:65])([CH3:66])[CH3:64]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Product 1

HCID 10053957HCID 10053957, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the indole carboxylic acid (360 mg, 0.93 mmol) in 4 mL of DMF was added Hunig's base (418 uL, 2.4 mmol). After 5 min, HATU (439 mg, 1.12 mmol) and HOAt (12 mg, 0.09 mmol) were added and then N-(3-amino-5-tert-butyl-2-methoxyphenyl)-methanesulfonamide (253 mg, 0.93 mmol). The mixture was stirred overnight. The reaction mixture was diluted with EtOAc, washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (1:2 hexanes-EtOAc) to give 390 mg of the desired amide.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (1:2 hexanes-EtOAc)

Sources & evidence

ORD record
ord-c4773594f8aa4951ac782ddebecf1e54
Source dataset
uspto-grants-2008_02
Patent number
US07335657B2

Reaction notes

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