Diisopropylamine → HCID 10053338, compound

HRID 1986652Notes

Reaction equation

HRID 1986652 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][C:10]2[C:15]3[S:16][C:17]([C:19]([OH:21])=O)=[CH:18][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:2]=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.C1C=CC2N(O)N=NC=2C=1.C(NC(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[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:19]([C:17]2[S:16][C:15]3[C:10]([NH:9][C:7](=[O:8])[C:3]4[CH:4]=[CH:5][CH:6]=[N:1][CH:2]=4)=[CH:11][CH:12]=[CH:13][C:14]=3[CH:18]=2)=[O:21])[CH:28]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 757711-HydroxybenzotriazoleHCID 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 57722436HCID 57722436, compound

Product 1

HCID 10053338HCID 10053338, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above carboxylic acid (100 mg, 0.335 mmol) and N-(3-amino-5-tert-butyl-2-methoxyphenyl)-methanesulfonamide (91 mg, 0.335 mmol) were dissolved in 2 mL DMF and stirred at room temperature. After about 10 min, HATU (127 mg, 0.335 mmol) and HOBt (45 mg, 0.335 mmol) were added followed by diisopropylamine (87 mg, 0.670 mmol, 120 uL) and the solution was stirred at room temperature. After stirring for eight days, the entire reaction was partitioned between EtOAc (75 mL) and water (50 mL). The layers were separated and the organic portion was washed with water (2×25 mL), brine (25 mL), dried (MgSO4), filtered and the solvent was removed to afford a tan solid. Column chromatography (EtOAc, silica gel) afforded the title compound as a colorless solid (105 mg, 57%).

Workup

  1. stirringthe solution was stirred at room temperature
  2. stirringAfter stirring for eight days
  3. customthe entire reaction
  4. customwas partitioned between EtOAc (75 mL) and water (50 mL)
  5. customThe layers were separated
  6. washthe organic portion was washed with water (2×25 mL), brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed
  10. customto afford a tan solid

Sources & evidence

ORD record
ord-713cfe73ac9d423b841b689ca83d1cc7
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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