Diisopropylethylamine → HCID 57635068, compound

HRID 2111424Notes

Reaction equation

HRID 2111424 reaction equation
[CH:1]1([N:7]2[CH2:13][CH:12]([CH3:14])[C:11](=[O:15])[N:10]([CH3:16])[C:9]3[CH:17]=[N:18][C:19]([N:21]([CH3:33])[C:22]4[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.C(N(C(C)C)C(C)C)C.[NH2:67][CH:68]1[CH2:73][CH2:72][N:71]([CH3:74])[CH2:70][CH2:69]1>CN(C)C=O>[CH:1]1([N:7]2[CH2:13][CH:12]([CH3:14])[C:11](=[O:15])[N:10]([CH3:16])[C:9]3[CH:17]=[N:18][C:19]([N:21]([CH3:33])[C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:67][CH:68]5[CH2:73][CH2:72][N:71]([CH3:74])[CH2:70][CH2:69]5)=[O:28])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 68907140HCID 68907140, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 57635068HCID 57635068, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.058 g (0.00013 mole) of (rac)-4-[(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)-methyl-amino]-3-methoxy-benzoic acid, 0.054 g (0.00014 mole) of 1-[bis(dimethylamino)-methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate and 3 mL of N,N-dimethylformamide was added 0.030 mL (0.00019 mole) of ethyldiisopropylamine. The mixture was stirred at room temperature for 30 minutes and then 0.022 g (0.00019 mole) of 4-amino-1-methyl-piperidine was then added. The mixture was stirred at room temperature for 3 hours and was then partitioned between ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed successively with water and brine, dried anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (100:0-75-25) to give 0.070 g of (rac)-4-[(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)-methyl-amino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (I-66) as white powder. HRMS (ES+) m/z Calcd for C30H43N7O3+H [(M+H)+]: 550.3500. Found: 550.3504.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. customwas then partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phases were washed successively with water and brine, dried anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane-methanol (100:0-75-25)

Sources & evidence

ORD record
ord-83ee32f2ee814f22b3e298a3fe68caea
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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