2-(Dimethylamino)ethanol → HCID 22405484, compound

HRID 441191Notes

Reaction equation

HRID 441191 reaction equation
[C:1]([C:4]1[CH:41]=[CH:40][C:7]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl.[CH3:43][N:44]([CH3:53])[CH2:45][CH2:46]CN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN(C)CCO>O1CCCC1.C(OCC)(=O)C>[CH3:43][N:44]([CH3:53])[CH2:45][CH2:46][O:2][C:1]([C:4]1[CH:41]=[CH:40][C:7]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:33])([F:34])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10076806HCID 10076806, compound

Product 1

HCID 22405484HCID 22405484, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[3-(4-carboxybenzyloxycarbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.281 g) in dry tetrahydrofuran (5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0,141 g), 1-hydroxybenzotriazole hydrate (0,066 g) and 2-dimethylaminoethanol (0.06 mL). The reaction mixture was stirred overnight before it was diluted with ethyl acetate, washed (twice with saturated sodium bicarbonate solution, then brine), dried and evaporated before purification by chromatography, eluting with dichloromethane:methanol (97:3), to afford the title compound; TLC: Rf =O.18, dichlormethane:methanol (97:3); HPLC: tR =6.51, FR=1, column A, water:acetonitrile (3:2); MS: m/z=645(M+1).

Workup

  1. washwashed (twice with saturated sodium bicarbonate solution
  2. dry with materialbrine), dried
  3. customevaporated before purification by chromatography
  4. washeluting with dichloromethane:methanol (97:3)

Sources & evidence

ORD record
ord-612313e73b8f4daaba8b4e6b5f3736dd
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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