1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89926841, compound

HRID 1522082Notes

Reaction equation

HRID 1522082 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.[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([Cl:33])[C:24]=1[N:34]1[S:39](=[O:41])(=[O:40])[N:38]([CH2:42][C:43](O)=[O:44])[CH2:37][CH:36]([CH3:46])[CH2:35]1.CCN=C=NCCCN(C)C.[CH:58]1[CH:63]=[C:62]2[N:64]=NN(O)[C:61]2=[CH:60][CH:59]=1.[OH2:68]>CS(C)=O.CC(O)C>[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[C:25]([Cl:33])[C:24]=1[N:34]1[S:39](=[O:40])(=[O:41])[N:38]([CH2:42][C:43]([NH:64][CH:62]2[CH:61]3[CH2:60][C:59]4([C:19]([NH2:15])=[O:68])[CH2:10][CH:8]([CH2:7][CH:63]2[CH2:58]4)[CH2:9]3)=[O:44])[CH2:37][C@H:36]([CH3:46])[CH2:35]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 64150Amantadine HydrochlorideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 86708929HCID 86708929, compound

Product 1

HCID 89926841HCID 89926841, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Procedure

To adamantyl amine hydrochloride (74 mg, 0.32 mmol) in DMSO (800 mg), were successively added DIPEA (208 mg, 1.60 mmol), i-PrOH (25 mL), 2-(6-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl) acetic acid (160 mg, 0.38 mmol), EDCI (123 mg, 0.64 mmol) and HOBt monohydrate (124 mg, 0.64 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 (113 mg, 49%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.69 (s, 1H), 7.65 (s, 1H), 6.95 (d, 1H, J=6.8 Hz), 5.58 (s, 1H), 5.29 (s, 1H), 4.40-4.34 (m, 1H), 4.12-3.90 (m, 3H), 3.78-3.72 (m, 1H), 3.33-3.21 (m, 2H), 2.62-2.59 (m, 1H), 2.14-1.58 (m, 13H), 0.97 (d, 3H, J=6.0 Hz). LC/MS MH+ 597

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 (113 mg, 49%, white solid)

Sources & evidence

ORD record
ord-dde2191c36d34128b43935a65ee63597
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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