Hydrogen Bromide → (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine

HRID 446911Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[S:13][C:12]3=[N:14][N:15]=[C:16]([C@H:17]([NH:19]C(=O)OCC4C=CC=CC=4)[CH3:18])[N:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br>C(O)(=O)C.O>[NH2:19][C@@H:17]([C:16]1[N:11]2[C:12]([S:13][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:10]2)=[N:14][N:15]=1)[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

(Step 8-iii) To a slurry of (R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate (0.39 g, 0.92 mmol) in acetic acid (20 mL) was added 48% hydrobromic acid in water (10 mL). The mixture was heated to 90° C. for 2 hours. After cooling to room temperature, the resulting solution was concentrated to ⅓ the original volume, poured on ice and the pH adjusted to 8 with 2N sodium hydroxide. The resulting precipitate was filtered, washed with water, and dried overnight in vacuo to provide (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine (0.19 g): ESMS MH+=294.

Workup

temperatureAfter cooling to room temperature
concentrationthe resulting solution was concentrated
additionpoured on ice
filtrationThe resulting precipitate was filtered
washwashed with water
customdried overnight in vacuo

Sources & evidence

ORD record: ord-6446ea2ea20d4ac58d1082da7b13e87c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481538B2

Reaction notes

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