Ammonia → HCID 59822068, compound

HRID 2063333Notes

Reaction equation

HRID 2063333 reaction equation
[N:1]1([C:7](=[O:33])[CH2:8][CH2:9][CH2:10][C@@H:11]2[C@H:16]3[C@H:17]4[C@H:26]([CH2:27][CH2:28][C@:14]3([CH3:15])[C:13](=[O:32])[CH2:12]2)[C:25]2[C:20](=[CH:21][C:22]([C:29]([OH:31])=O)=[CH:23][CH:24]=2)[CH2:19][CH2:18]4)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N.C[N:36]1CCOCC1.OC1C2N=NNC=2C=CC=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[N:1]1([C:7](=[O:33])[CH2:8][CH2:9][CH2:10][C@@H:11]2[C@H:16]3[C@H:17]4[C@H:26]([CH2:27][CH2:28][C@:14]3([CH3:15])[C:13](=[O:32])[CH2:12]2)[C:25]2[C:20](=[CH:21][C:22]([C:29]([NH2:36])=[O:31])=[CH:23][CH:24]=2)[CH2:19][CH2:18]4)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59822061HCID 59822061, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 59822068HCID 59822068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

430 mg 15α-(4-morpholin-4-yl-4-oxobutyl)-17-oxoestra-1(10),2,4-triene-3-carboxylic acid is dissolved in DCM. 3 eq NH3 solution (0.5 M in 1,4 dioxane), 3 eq 4-methyl morpholine, 1.75 eq hydroxybenztriazole and 2 eq EDCl are added slowly in an ice-bath. After stirring at RT for a couple of hours, the reaction mixture is left over night without stirring. The mixture is extracted twice with NaHCO3 (5% in H2O), twice with 1M KHSO4 and with brine. The combined organic layers are dried (Na2SO4) and the solvent removed. Purifying by column chromatography (EtOAc/EtOH, 25:1) gives 135 mg pure 15α-(4-morpholin-4-yl-4-oxobutyl)-17-oxoestra-1(10),2,4-triene-3-carboxamide (EXAMPLE 1)

Workup

  1. waitthe reaction mixture is left over night
  2. stirringwithout stirring
  3. extractionThe mixture is extracted twice with NaHCO3 (5% in H2O), twice with 1M KHSO4 and with brine
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customthe solvent removed
  6. customPurifying by column chromatography (EtOAc/EtOH, 25:1)

Sources & evidence

ORD record
ord-24bc050d766a46cca6f6b46cd664a0d3
Source dataset
uspto-grants-2012_10
Patent number
US08288367B2

Reaction notes

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