Sodium Hydroxide → 1-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea

HRID 1685053Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]O)[N:14]=1)=[O:8].[NH2:20][C:21]1SC=C(COC(=O)C)N=1.FC1C=C(C=CC=1)[CH2:35][N:36]=C=O.[OH-].[Na+]>C1COCC1.CCOC(C)=O.CO>[C:21]([CH:15]([NH:36][CH3:35])[C:13]1[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=2)=[O:8])[S:11][CH:12]=1)#[N:20]

Participants

Conditions

Temperature: 60 °C

Procedure

Preparation of -(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea. To a solution of acetic acid 2-amino-thiazol-4-ylmethyl ester (6.89 g) in THF (50 mL) were 3-fluorobenzylisocyanate (5.50 g) and TEA (5.03 mL) added. The resultant solution was heated at 70° C. over 2 h. Then, MeOH (30 mL) and NaOH (6N, 15 mL) were added to the above solution. The reaction mixture was heated at 60° C. for 30 min After cooling down, the reaction mixture was diluted with EtOAc (150 mL) and was washed with water. The organic solvents were concentrated and the residue was purified by silica-gel column chromatography to afford 8.29 g of the desired product-1-(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea.

Workup

additionadded
temperatureAfter cooling down
washwas washed with water
concentrationThe organic solvents were concentrated
customthe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record: ord-0ca05ccaa8d84add919c842cf41e17a6
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148380B2

Reaction notes

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