Isopropanol → HCID 86708935, compound

HRID 1522085Notes

Reaction equation

HRID 1522085 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.[F:22][C:23]1([F:44])[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:56]1[CH:57]=[CH:58][C:59]2[N:64](O)N=N[C:60]=2[CH:61]=1.CC([OH:69])C>CS(C)=O>[F:44][C:23]1([F:22])[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]([NH:64][CH:59]2[CH:58]3[CH2:57][C:56]4([C:19]([NH2:15])=[O:69])[CH2:10][CH:8]([CH2:7][CH:60]2[CH2:61]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 86708933HCID 86708933, compound

Product 1

HCID 86708935HCID 86708935, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To adamantyl amine hydrochloride (16 mg, 0.07 mmol) in DMSO (500 mg), were successively added DIPEA (46 mg, 0.35 mmol), i-PrOH (5 mL), 2-(4,4-difluoro-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid (33 mg, 0.08 mmol), EDCI (27 mg, 0.14 mmol) and HOBt (21 mg, 0.14 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 (10 mL), kept to stand for 1 hr for crystallization, filtered and washed three times with water (10 mL). The filtered solid was purified by column chromatography (dichloromethane:methanol=97:3) to yield the compound of interest (18 mg, 38%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.44 (s, 2H), 6.67 (d, 1H J=8.0 Hz), 5.54 (s, 1H), 5.24 (s, 1H), 4.21 (s, 2H), 4.14-4.01 (m, 5H), 2.10-1.56 (m, 13H).

Workup

  1. concentrationAfter concentration at 50° C. under reduced pressure
  2. additionthe resultant was added with saturated NH4Cl solution (10 mL)
  3. customto stand for 1 hr for crystallization
  4. filtrationfiltered
  5. washwashed three times with water (10 mL)
  6. customThe filtered solid was purified by column chromatography (dichloromethane:methanol=97:3)
  7. customto yield the compound of interest (18 mg, 38%, white solid)

Sources & evidence

ORD record
ord-99a09300fe5948d0825f8cd003ddd468
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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