Diisopropylethylamine → HCID 59473707, compound

HRID 453918Notes

Reaction equation

HRID 453918 reaction equation
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:34]([O:38][C:39]([NH:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[C:47]2[C:51]=1[N:50]([CH2:52][C:53]([OH:55])=O)[CH:49]=[CH:48]2)=[O:40])([CH3:37])([CH3:36])[CH3:35].[N:56]1[CH:61]=[CH:60][C:59]([N:62]2[CH2:67][CH2:66][C:65]3([CH2:72][CH2:71][NH:70][CH2:69][CH2:68]3)[CH2:64][CH2:63]2)=[CH:58][CH:57]=1>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[O:55]=[C:53]([N:70]1[CH2:69][CH2:68][C:65]2([CH2:66][CH2:67][N:62]([C:59]3[CH:60]=[CH:61][N:56]=[CH:57][CH:58]=3)[CH2:63][CH2:64]2)[CH2:72][CH2:71]1)[CH2:52][N:50]1[C:51]2[C:47](=[CH:46][CH:45]=[CH:44][C:43]=2[CH2:42][NH:41][C:39](=[O:40])[O:38][C:34]([CH3:36])([CH3:37])[CH3:35])[CH:48]=[CH:49]1

Participants

8

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 159408113-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecaneHCID 59473691HCID 59473691, compound

Product 1

HCID 59473707HCID 59473707, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

HATU (464 mg, 1.22 mmol, 1.0 equiv.) and DIPEA (0.8 ml, 4.88 mmol, 4.0 equiv.) were added at 0° C. to a suspension of 2-(7-((tert-butoxycarbonylamino)methyl)-1H-indol-1-yl)acetic acid (372 mg, 1.22 mmol, 1.0 equiv.) in THF (8 ml), and the mixture was stirred for 15 min. A solution of 3-pyridin-4-yl-3,9-diazaspiro[5.5]undecane (F-14) (283 mg, 1.22 mmol, 1.0 equiv.), dissolved in a mixture of THF (4 ml) and DMF (0.5 ml), was added, and stirring was carried out for 14 h at RT. The reaction mixture was diluted with ethyl acetate (30 ml) and extracted with sodium bicarbonate solution (2×20 ml), NH4Cl solution (2×20 ml), water (20 ml) and sat. NaCl solution (20 ml) and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by column chromatography (Alox neutral; 0.5% MeOH/DCM), and the desired product was thus obtained in the form of a white solid.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas carried out for 14 h at RT
  4. extractionextracted with sodium bicarbonate solution (2×20 ml), NH4Cl solution (2×20 ml), water (20 ml) and sat. NaCl solution (20 ml)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum
  7. customthe crude product was purified by column chromatography (Alox neutral; 0.5% MeOH/DCM)

Sources & evidence

ORD record
ord-b45f05fb7331417ab315e0763a01ba2e
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

Loading…