4-Methylmorpholine → HCID 59822073, compound

HRID 2063336Notes

Reaction equation

HRID 2063336 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:33])[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(C(O)=O)=[CH:23][CH:24]=2)[CH2:19][CH2:18]4)=[N:4][CH:3]=1.C(NC)C[CH2:36][CH3:37].[CH3:40][N:41]1[CH2:46][CH2:45]O[CH2:43][CH2:42]1.C1C=CC2N([OH:56])N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:46]([N:41]([CH3:40])[C:42]([C:43]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[C@@H:26]1[C@H:17]([C@H:16]3[C@@:14]([CH2:28][CH2:27]1)([CH3:15])[C:13](=[O:32])[CH2:12][C@H:11]3[CH2:10][CH2:9][C:8]([NH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][N:4]=1)=[O:33])[CH2:18][CH2:19]2)=[O:56])[CH2:45][CH2:36][CH3:37]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8068N-MethylbutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59822071HCID 59822071, compound

Product 1

HCID 59822073HCID 59822073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 mg 15beta-{3-[(5-methyl-1,3-thiazol-2-yl)amino]-3-oxopropyl}-17-oxoestra-1(10),2,4-triene-3-carboxylic acid is dissolved in DCM. 2.5 eq N-Butylmethylamine (11.8 mg, 0.135 mmol), 3 eq 4-methyl morpholine, 1.7 eq HOBT and 2.2 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, 1:5) gives 21.1 mg pure N-butyl-N-methyl-15beta-{3-[(5-methyl-1,3-thiazol-2-yl)amino]-3-oxopropyl}-17-oxoestra-1(10),2,4-triene-3-carboxamide.

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, 1:5)

Sources & evidence

ORD record
ord-3c0ad401a73b4d37a72c3dd8d9724be0
Source dataset
uspto-grants-2012_10
Patent number
US08288367B2

Reaction notes

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