Trifluoroacetic acid → 5-(Piperidin-4-ylamino)-[1,3,4]thiadiazole-2-carbonitrile

HRID 1426376Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]([C:20]#[N:21])=[N:18][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[S:16][C:17]([C:20]#[N:21])=[N:18][N:19]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-(5-cyano-[1,3,4]thiadiazol-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (D5) (0.973 g, 3.12 mmol) in dichloromethane (55 ml), at 0° C., was added trifluoroacetic acid (3 ml). The reaction mixture was stirred at 0° C. for 1 h. and at room temperature for 18 h. more. After this period, the reaction mixture was extracted with a saturated solution of sodium carbonate. The aqueous layer was extracted with ethyl acetate (2×25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo to yield D6 (0.60 g, 92%) as a solid. C8H11N3S requires 209. Found 210 (MH+).

Workup

waitAfter this period
extractionthe reaction mixture was extracted with a saturated solution of sodium carbonate
extractionThe aqueous layer was extracted with ethyl acetate (2×25 ml)
customThe organic layer was separated
dry with materialdried (Na2SO4)
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-e11f633700ae4335bc69f19ddb3f6d82
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933101B2

Reaction notes

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