Diisopropylethylamine → HCID 67255234, compound

HRID 1509214Notes

Reaction equation

HRID 1509214 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:3]=1.CCN(C(C)C)C(C)C.Cl[CH:43]([CH3:47])[C:44](Cl)=[O:45].C(=O)(O)[O-].[Na+]>C1COCC1>[C:22]([O:21][C:20](=[O:26])[NH:19][C:15]1([C:12]2[CH:11]=[CH:10][C:9]([C:5]3[C:4]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:3][C:2]4[NH:1][C:44](=[O:45])[CH:43]([CH3:47])[O:8][C:7]=4[N:6]=3)=[CH:14][CH:13]=2)[CH2:18][CH2:17][CH2:16]1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1110192-Chloropropionyl chlorideHCID 516892Sodium BicarbonateHCID 67257668HCID 67257668, compound

Product 1

HCID 67255234HCID 67255234, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 1-(4-(5-amino-6-oxo-3-phenyl-1,6-dihydropyridin-2-yl)phenyl)cyclobutylcarbamate (0.5 g, 1.159 mmol) in THF (Volume: 20 ml) was added DIPEA (1.01 ml) followed by the addition of 2-chloropropanoyl chloride (0.235 g, 1.854 mmol) in THF (5 ml) in dropwise at 0 degree over 1 h. The resulted mixture was stirred at r.t. over night. Sodium bicarbonate saturated solution (30 ml) was added. The resulted mixture was heated to reflux for 16 h. The reaction mixture was cooled down to room temperature. The organic phase was separated. The aqueous phase was extracted with ethyl acetate (40 ml). The organic phase was combined and washed with water (30 mlX2), brine (25 ml) then concentrated at reduced pressure. The residue was suspended in DCM (10 ml). The precipitate was collected by filtration and washed with DCM (5 ml) to afford product (439 mg). 1H NMR (500 MHz, CD3OD): 7.20-7.29 (m, 8H), 7.13-7.15 (m, 2H), 4.98 (q, 1H), 2.41-2.47 (m, 4H), 2.05 (m, 1H), 1.86 (m, 1H), 1.64 (d, 3H), 1.21-1.36 (br, 9H).

Workup

  1. temperatureThe resulted mixture was heated
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. customThe organic phase was separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (40 ml)
  6. washwashed with water (30 mlX2), brine (25 ml)
  7. concentrationthen concentrated at reduced pressure
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with DCM (5 ml)

Sources & evidence

ORD record
ord-e57b273db4ba40be98d0243dd69667f8
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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