Dimethyl Sulfoxide → HCID 70683860, compound

HRID 1522074Notes

Reaction equation

HRID 1522074 reaction equation
Cl.C12(N)CC3[CH2:7][CH:8]([CH2:10]C(C3)C1)[CH2:9]2.CC[N:15]([CH:19](C)C)C(C)C.[O:22]=[S:23]1(=[O:44])[N:30]([C:31]2[C:36]([Cl:37])=[CH:35][C:34]([Cl:38])=[CH:33][C:32]=2[Cl:39])[CH2:29][C:26]2([CH2:28][CH2:27]2)[CH2:25][N:24]1[CH2:40][C:41](O)=[O:42].CCN=C=NCCCN(C)C.[CH:56]1[CH:57]=[CH:58][C:59]2[N:64](O)N=N[C:60]=2[CH:61]=1.CS(C)=[O:68]>CC(O)C>[O:22]=[S:23]1(=[O:44])[N:30]([C:31]2[C:36]([Cl:37])=[CH:35][C:34]([Cl:38])=[CH:33][C:32]=2[Cl:39])[CH2:29][C:26]2([CH2:27][CH2:28]2)[CH2:25][N:24]1[CH2:40][C:41]([NH:64][CH:59]1[CH:58]2[CH2:57][C:56]3([C:19]([NH2:15])=[O:68])[CH2:10][CH:8]([CH2:7][CH:60]1[CH2:61]3)[CH2:9]2)=[O:42]

Participants

8

Reactant 6

HCID 679Dimethyl SulfoxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 64150Amantadine HydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86708921HCID 86708921, compound

Product 1

HCID 70683860HCID 70683860, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To adamantyl amine hydrochloride (26 mg, 0.11 mmol) in DMSO (700 mg), were successively added DIPEA (78 mg, 0.60 mmol), i-PrOH (10 mL), 2-(6,6-dioxido-7-(2,4,6-trichlorophenyl)-6-thia-5,7-diazaspiro[2.5]octane-5-yl)acetic acid (50 mg, 0.13 mmol), EDCI (46 mg, 0.22 mmol) and HOBt (37 mg, 0.22 mmol), and agitated for 12 hr at room temperature. After concentration at 50° C. under reduced pressure, the resultant was added with saturated NH4Cl solution (20 mL), kept to stand for 1 hr for crystallization, filtered and washed three times with water (20 mL). The filtered solid was purified by column chromatography (dichloromethane:methanol=97:3) to yield the compound of interest (40 mg, 63%, white solid).

Workup

  1. concentrationAfter concentration at 50° C. under reduced pressure
  2. additionthe resultant was added with saturated NH4Cl solution (20 mL)
  3. customto stand for 1 hr for crystallization
  4. filtrationfiltered
  5. washwashed three times with water (20 mL)
  6. customThe filtered solid was purified by column chromatography (dichloromethane:methanol=97:3)
  7. customto yield the compound of interest (40 mg, 63%, white solid)

Sources & evidence

ORD record
ord-04b1397c9d0a443b9137116ac2122cfe
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

Loading…