Diisopropylethylamine → HCID 21097218, compound

HRID 2109315Notes

Reaction equation

HRID 2109315 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=[CH:12]1.[NH2:22][C:23]1[C:24]([O:38][CH3:39])=[C:25]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:29]([C:27]1[CH:26]=[C:25]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:24]([O:38][CH3:39])=[C:23]([NH:22][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N:11]3[CH:15]=[C:14]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[N:13]=[CH:12]3)[CH:4]=2)[CH:28]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 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)-methanesulfonamideHCID 21097332HCID 21097332, compound

Product 1

HCID 21097218HCID 21097218, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-benzoic acid (15 mg; 0.054 mmol), N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methane-sulfonamide (29 mg; 0.11), and HATU (49 mg; 0.11 mmol) were dissolved in 1 mL of DMF, and the mixture was chilled to 0° C. Diisopropylethylamine (19 μL; 0.11 mmol) was then added, the cold-bath was removed, and the mixture was stirred overnight. The mixture was then poured into water and extracted with EtOAc. The organic portion was washed with NaHCO3 and brine, and the washes were extracted once with EtOAc. The extracts were combined, dried with Na2SO4, filtered, and concentrated. Chromatography (0-6.5% MeOH/0.5% NH4OH in CH2Cl2) provided 23 mg (0.043 mmol; 80%) of Example 160. ESI MS m/z 534 [C28H31N5O4S+H]+.

Workup

  1. customthe cold-bath was removed
  2. additionThe mixture was then poured into water
  3. extractionextracted with EtOAc
  4. washThe organic portion was washed with NaHCO3 and brine
  5. extractionthe washes were extracted once with EtOAc
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography (0-6.5% MeOH/0.5% NH4OH in CH2Cl2) provided 23 mg (0.043 mmol; 80%) of Example 160

Sources & evidence

ORD record
ord-554c081abf51448086f5951e6a1e092d
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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