Isopropanol → HCID 70688125, compound

HRID 1522071Notes

Reaction equation

HRID 1522071 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.[CH2:22]=[C:23]1[CH2:28][N:27]([C:29]2[C:34]([Cl:35])=[CH:33][C:32]([Cl:36])=[CH:31][C:30]=2[Cl:37])[S:26](=[O:39])(=[O:38])[N:25]([CH2:40][C:41](O)=[O:42])[CH2:24]1.CCN=C=NCCCN(C)C.[CH:55]1[CH:56]=[CH:57][C:58]2[N:63](O)N=N[C:59]=2[CH:60]=1.CC([OH:68])C>CS(C)=O>[CH2:22]=[C:23]1[CH2:28][N:27]([C:29]2[C:30]([Cl:37])=[CH:31][C:32]([Cl:36])=[CH:33][C:34]=2[Cl:35])[S:26](=[O:39])(=[O:38])[N:25]([CH2:40][C:41]([NH:63][CH:58]2[CH:57]3[CH2:56][C:55]4([C:19]([NH2:15])=[O:68])[CH2:10][CH:8]([CH2:7][CH:59]2[CH2:60]4)[CH2:9]3)=[O:42])[CH2:24]1

Participants

8

Reactant 6

HCID 3776IsopropanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 64150Amantadine HydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86708919HCID 86708919, compound

Product 1

HCID 70688125HCID 70688125, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To adamantyl amine hydrochloride (127 mg, 0.55 mmol) in DMSO (700 mg), were successively added DIPEA (357 mg, 2.75 mmol), i-PrOH (10 mL), 2-(4-methylene-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid (253 mg, 0.66 mmol), EDCI (211 mg, 1.10 mmol) and HOBt (169 mg, 1.10 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 (122 mg, 39%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 2H), 6.93 (d, 1H J=8.0 Hz), 5.58 (s, 1H), 5.29 (m, 2H), 5.21 (s, 1H), 4.29 (s, 2H), 4.26 (s, 2H), 4.06 (m, 1H), 3.97 (s, 2H), 2.17-1.58 (m, 13H).

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 (122 mg, 39%, white solid)

Sources & evidence

ORD record
ord-c4cd91adc75a4d7395df1dc12a840467
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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