Diisopropylethylamine → HCID 68504170, compound

HRID 1713989Notes

Reaction equation

HRID 1713989 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([OH:23])=O)[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][NH:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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>C(Cl)Cl.Cl>[CH:1]1([C:7]2[C:15]3[CH:10]=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][C:14]=3[N:9]3[CH2:20][C:21](=[O:23])[N:31]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[CH2:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[C:8]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68505199HCID 68505199, compound

Product 1

HCID 68504170HCID 68504170, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-6-(methoxycarbonyl)-1H-indol-1-yl]acetic acid in DCM (0.08 M), DIPEA (3.5 eq) and HATU (2.5 eq) were added and the mixture stirred at RT overnight. The solution was diluted with DCM and HCl (1N) and the 2 phases separated. The aqueous phase was extracted with DCM (2×). The combined organic phases were then washed with a saturated aqueous solution of NaHCO3 and brine before being dried over Na2SO4, filtered and concentrated in vacuo. The crude was then used in the next step without further purification; MS (ES+) m/z 474 (M+H)+

Workup

  1. customthe 2 phases separated
  2. extractionThe aqueous phase was extracted with DCM (2×)
  3. washThe combined organic phases were then washed with a saturated aqueous solution of NaHCO3 and brine
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was then used in the next step without further purification

Sources & evidence

ORD record
ord-0d1502f5036a4614bbfcd404a5edc478
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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