1-Hydroxybenzotriazole → HCID 178482473, compound

HRID 1620506Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([OH:13])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[CH3:38][NH:39][C:40]1=[N:41][C:42](=[O:52])[S:43]/[C:44]/1=[CH:45]\[CH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>CN(C)C=O.O.C(N(CC)CC)C>[CH3:38][NH:39][C:40]1=[N:41][C:42](=[O:52])[S:43]/[C:44]/1=[CH:45]\[CH:46]1[CH2:51][CH2:50][N:49]([C:11]([C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])=[O:13])[CH2:48][CH2:47]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-methyl-1-benzofuran-2-carboxylic acid (19.4 mg) in N,N-dimethylformamide (1 mL) were added 1-hydroxybenzotriazole (16.2 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23 mg), and the mixture was stirred at 0° C. for 5 min. To the reaction mixture were added triethylamine (0.28 mL) and (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (29.8 mg), and the mixture was further stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the precipitate was collected by filtration, and washed with water and diisopropyl ether to give the title compound (19.3 mg).

Workup

stirringthe mixture was further stirred at room temperature for 5 hr
filtrationthe precipitate was collected by filtration
washwashed with water and diisopropyl ether

Sources & evidence

ORD record: ord-f7f2c43d813340dab9155750bcee77d6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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