Phenyl Isothiocyanate → HCID 178514008, compound

HRID 591958Notes

Reaction equation

HRID 591958 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[N:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:22]=S.N=C=N>O1CCCC1>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:22]([NH:21][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 160435CarbodiimideHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178514008HCID 178514008, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100 mg, 0.5 mmol), isothiocyanatobenzene (60 L, 0.5 mmol), and PS-carbodiimide (769 mg, 1.01 mmol) were heated overnight at 70° C. in a sealed tube with tetrahydrofuran (10 mL). The solids were removed by filtration and the filtrate was concentrated. The organics were purified by reverse phase chromatography (Gilson) to afford, following neutralization and concentration, the title compound as a yellow solid (21%). 1H NMR (d-4 methanol): 7.73 (m, 3H), 7.29 (m, 2H), 6.98 (m, 1H), 6.44 (m, 1H), 6.40 (m, 1H), 5.31 (m, 1H), 4.88 (m, 3H), 2.98 (s, 1H), 2.89 (s, 1H), 2.73 (m, 1H), 2.37 (m, 1H), 1.57 (m, 1H), 1.30 (m, 2H). MS: 394.9 (M+H). HPLC retention time: 2.33 minutes (G Method).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe organics were purified by reverse phase chromatography (Gilson)
  4. customto afford
  5. concentrationneutralization and concentration

Sources & evidence

ORD record
ord-27f480bf29dd45d8b49bfab121139e65
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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