Ammonia → HCID 25115738, compound

HRID 2063335Notes

Reaction equation

HRID 2063335 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:22]([C:29](O)=[O:30])=[CH:23][CH:24]=2)[CH2:19][CH2:18]4)=[N:4][CH:3]=1.N.C[N:36]1CCOCC1.OC1C2N=NNC=2C=CC=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[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:22]([C:29]([NH2:36])=[O:30])=[CH:23][CH:24]=2)[CH2:19][CH2:18]4)=[N:4][CH:3]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59822071HCID 59822071, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 25115738HCID 25115738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g 15β-{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. 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 and the reaction is carried out as described in Example 1. Purification by column chromatography (EtOAc/EtOH, 6:1) gives pure 15β-{3-[(5-methyl-1,3-thiazol-2-yl)amino]-3-oxopropyl}-17-oxoestra-1(10),2,4-triene-3-carboxamide (EXAMPLE 3)

Workup

  1. customPurification by column chromatography (EtOAc/EtOH, 6:1)

Sources & evidence

ORD record
ord-cad1be0a083a4b08bc53d64bbee9b67a
Source dataset
uspto-grants-2012_10
Patent number
US08288367B2

Reaction notes

Loading…