Triethylamine → HCID 178485247, compound

HRID 555112Notes

Reaction equation

[C:1]([C:3]1([NH:6][C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:35])=[C:13]([C:15]3[CH:16]=[CH:17][C:18]4[O:22][C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)=[C:20]([C:30]([NH:32][CH3:33])=[O:31])[C:19]=4[CH:34]=3)[CH:14]=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:37][OH:38].CCN(CC)CC>C(O)C>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:21]2[O:22][C:18]3[CH:17]=[CH:16][C:15]([C:13]4[CH:14]=[C:9]([C:7](=[O:8])[NH:6][C:3]5([C:1](=[NH:2])[NH:37][OH:38])[CH2:4][CH2:5]5)[CH:10]=[CH:11][C:12]=4[CH3:35])=[CH:34][C:19]=3[C:20]=2[C:30]([NH:32][CH3:33])=[O:31])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a mixture of 5-(5-(1-cyanocyclopropylcarbamoyl)-2-methylphenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (43.5 mg, 0.093 mmol) in ethanol (1.5 mL) at r.t. under N2 was added hydroxylamine hydrochloride (12.93 mg, 0.186 mmol), followed by Et3N (0.039 mL, 0.279 mmol). The mixture was stirred at reflux (115° C.) for about 4 hours. The mixture was cooled to r.t. and evaporated. The residue was used for the next step without further purification. LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters MICROMASS®. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=5 ml/min, Column: PHENOMENEX® Luna, 3.0×50 mm, S10; (ES+) m/z (M+H)+=501.13, HPLC Rt=1.385 min.

Workup

temperatureThe mixture was cooled to r.t.
customevaporated
customThe residue was used for the next step without further purification
customB=100, Gradient time=2 min
customtime=3 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record: ord-090d700702b14251ae6fc3a625af0348
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048887B2

Reaction notes

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