Potassium cyanate → N-{2-(Carbamoylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide

HRID 220699

Reaction equation

Cl.[NH2:2][CH2:3][CH:4]([NH:15][C:16](=[O:38])[CH2:17][N:18]1[C:22](=[O:23])[N:21]([CH2:24][C@H:25]([OH:30])[C:26]([F:29])([F:28])[F:27])[C:20]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[N:19]1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.[O-:39][C:40]#[N:41].[K+]>CO.O>[C:40]([NH:2][CH2:3][CH:4]([NH:15][C:16](=[O:38])[CH2:17][N:18]1[C:22](=[O:23])[N:21]([CH2:24][C@H:25]([OH:30])[C:26]([F:29])([F:27])[F:28])[C:20]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[N:19]1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:14])[F:13])[CH:6]=1)(=[O:39])[NH2:41]

Participants

Conditions

Temperature: 40 °C

Procedure

Of the compound from Example 12, 180 mg (0.31 mmol) were introduced in 3 ml of methanol/water 1:1 and admixed with potassium cyanate (75 mg, 0.92 mmol) at RT. The mixture was heated at 40° C. for 90 min. The methanol was removed on a rotary evaporator and the aqueous residue was diluted with 20 ml of water. The precipitated solid was isolated by filtration, washed with a little water and dried in an HV. This gave 146 mg (76% of theory) of the title compound.

Workup

customThe methanol was removed on a rotary evaporator
additionthe aqueous residue was diluted with 20 ml of water
customThe precipitated solid was isolated by filtration
washwashed with a little water
customdried in an HV

Sources & evidence

ORD record: ord-097d725475ae4cc2b6b4909ae6880d54
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202895B2

Linked notes

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