Ammonia → HCID 69207807, compound

HRID 30729Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([OH:30])[C:27]([OH:29])=O)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.[C:31](Cl)(=[O:35])[O:32][CH2:33][CH3:34].C(N(CC)CC)C.[NH3:44]>C(OCC)(=O)C>[CH2:33]([O:32][C:31]([O:30][CH:26]([CH2:25][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16](=[O:17])/[CH:15]=[CH:14]/[C:9]2[CH:10]=[N:11][N:12]([CH3:13])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:24][CH:23]=1)[C:27]([NH2:44])=[O:29])=[O:35])[CH3:34]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]-2-hydroxypropionic acid (409 mg), ethyl chlorocarbonate (324 mg), triethylamine (405 mg) and ethyl acetate (10 ml) was stirred at 0° C. for 1 hr. Conc. aqueous ammonia (10 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the precipitated solids were collected by filtration, washed with water and dried to give 2-(ethoxycarbonyloxy)-3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)phenyl]propionamide (471 mg, 98%) as colorless crystals.

Workup

stirringthe mixture was stirred at room temperature for 1 hr
concentrationThe reaction mixture was concentrated
filtrationthe precipitated solids were collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-9c112cdaed2a4a87b59aeb3f3d5a9981
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423159B2

Reaction notes

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