Diisopropylethylamine → HCID 58382191, compound

HRID 1628058Notes

Reaction equation

HRID 1628058 reaction equation
[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=4)[C:17]([OH:19])=O)[N:11]([S:23]([C:26]4[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:66]1[CH2:71][CH2:70][N:69]([CH2:72][CH2:73][NH2:74])[CH2:68][CH2:67]1>CCOC(C)=O.CN(C=O)C>[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=4)[C:17]([NH:74][CH2:73][CH2:72][N:69]4[CH2:70][CH2:71][O:66][CH2:67][CH2:68]4)=[O:19])[N:11]([S:23]([C:26]4[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=4)(=[O:24])=[O:25])[C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58382133HCID 58382133, compound

Product 1

HCID 58382191HCID 58382191, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A flask was charged with 3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzoic acid (0.10 g, 0.22 mmol, prepared using D from Preparation #1 with 3-boronobenzoic acid), DIEA (0.039 mL, 0.224 mmol), HATU (0.085 g, 0.224 mmol) and DMF (3 mL). The mixture was stirred at about 40° C. for about 30 min. To the mixture was added 2-morpholinoethanamine (0.038 mL, 0.291 mmol). The mixture was allowed to stir at about 40° C. for about 2 h. The mixture was stirred overnight at rt and then diluted with EtOAc (10 mL) and washed with water (10 mL). The aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with an elution gradient of 0 to 7.5% MeOH/DCM to give 3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzamide (0.123 g, 98%): LC/MS (Table 2, Method c) Rt=1.20 min; MS m/z 559 (M+H)+.

Workup

  1. stirringto stir at about 40° C. for about 2 h
  2. stirringThe mixture was stirred overnight at rt
  3. washwashed with water (10 mL)
  4. extractionThe aqueous layer was further extracted with EtOAc (2×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography with an elution gradient of 0 to 7.5% MeOH/DCM

Sources & evidence

ORD record
ord-c815fb88c391424ab15ac0c06c60a6d3
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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