Diisopropylethylamine → HCID 68509324, compound

HRID 1714063Notes

Reaction equation

HRID 1714063 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][CH3:33])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C:23](O)=O)[CH2:18][C:17]4[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=4[C:15]=23)[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.[CH3:67][NH:68][CH2:69][C:70]1[CH:71]=[N:72][CH:73]=[CH:74][CH:75]=1.[Cl-].[Na+].[OH2:78]>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][CH3:33])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]([N:68]([CH3:67])[CH2:69][C:70]4[CH:71]=[N:72][CH:73]=[CH:74][CH:75]=4)=[O:78])[CH2:18][C:29]4[CH:28]=[CH:27][CH:26]=[CH:17][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 883933-(Methylaminomethyl)pyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57417360Sodium chloride; waterHCID 68510603HCID 68510603, compound

Product 1

HCID 68509324HCID 68509324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [14-cyclohexyl-11-(methoxycarbonyl)-7,8-dihydroindolo[2,1-a][2,5]benzodiazocin-6(5H)-yl]acetic acid in DCM (0.05 M), 3.5 eq of DIPEA, 1.5 eq of HATU and 1.5 eq of N-methyl-1-pyridin-3-ylmethanamine were added and the mixture was stirred overnight at RT. The solution was portioned between DCM and brine. The aqueous phase was re-extracted with DCM (twice) and the combined organics then dried over Na2SO4, filtered and concentrated in vacuo. The crude was used in the next step without further purification; MS (ES+) m/z 551 (M+H)+.

Workup

  1. extractionThe aqueous phase was re-extracted with DCM (twice) and the combined organics
  2. dry with materialthen dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was used in the next step without further purification

Sources & evidence

ORD record
ord-d15a667cce224826bde2e5b04fdcb03d
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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