Diisopropylethylamine → HCID 46909184, compound

HRID 1694316Notes

Reaction equation

HRID 1694316 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=[C:18]3[CH:17]1[CH2:25][C:26]([OH:28])=O)(=[O:15])=[O:14])[CH:7]=[CH:6]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:62]([NH:66][CH2:67][C:68]1[CH:69]=[C:70]2[C:75](=[CH:76][CH:77]=1)[CH2:74][CH:73]([NH2:78])[CH2:72][CH2:71]2)([CH3:65])([CH3:64])[CH3:63]>C(Cl)Cl>[C:62]([NH:66][CH2:67][C:68]1[CH:69]=[C:70]2[C:75](=[CH:76][CH:77]=1)[CH2:74][CH:73]([NH:78][C:26](=[O:28])[CH2:25][CH:17]1[N:16]([S:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=3)(=[O:14])=[O:15])[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=[C:18]13)[CH2:72][CH2:71]2)([CH3:65])([CH3:63])[CH3:64]

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 594864212-(2-(6-Methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acidHCID 59486444HCID 59486444, compound

Product 1

HCID 46909184HCID 46909184, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) suspension of 2-(2-(6-methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid (S2) (310 mg, 0.77 mmol, 1.0 eq.) in DCM (20 ml) was added HATU (600 mg, 1.54 mmol, 2 eq.) and DIPEA (0.4 ml, 2.31 mmol, 3 eq.) and the reaction mixture was allowed to stir for 30 min. Finally, 6-((tert-Butylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-amine (A15) (180 mg, 0.77 mmol, 1.0 eq.) was added and the reaction mixture and it was stirred at RT for 16 h. The mixture was diluted with DCM (100 ml) and successively washed with ammonium chloride solution (50 ml), sodium bicarbonate solution (50 ml), water (10 ml) and brine (10 ml). The organics were dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica gel, 6% MeOH/DCM) to yield the pure title compound as a white solid. Yield: 34% (160 mg, 0.26 mmol); MS, Rt=3.6 min; m/z=615.1 [MH]+

Workup

  1. temperatureTo a cooled
  2. stirringthe reaction mixture and it was stirred at RT for 16 h
  3. washsuccessively washed with ammonium chloride solution (50 ml), sodium bicarbonate solution (50 ml), water (10 ml) and brine (10 ml)
  4. dry with materialThe organics were dried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customto give the crude product which
  7. customwas purified by column chromatography (silica gel, 6% MeOH/DCM)

Sources & evidence

ORD record
ord-0d809fd21b3446dfa74c21ae09aaaa15
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

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