Phenylacetyl chloride → HCID 25212773, compound

HRID 2382786Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]3[N:12]=[C:13]([NH2:15])[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[CH:2]1.[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]3[N:12]=[C:13]([NH:15][C:23](=[O:24])[CH2:22][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[CH:2]1

Participants

Reactant 2

HCID 7679Phenylacetyl chloride

HCID 252159385-(Furan-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25212773HCID 25212773, compoundYield 33%

Procedure

The title compound was prepared following procedure described for intermediate B1, but starting from 5-(3-furyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A2), 41 mg; 0.20 mmol; 1.0 eq.) and phenylacetyl chloride (38 μl; 0.41 mmol; 2.0 eq). Purification of the compound by flash chromatography on silica (EtOAc/c-Hex, 50:50) gave the title compound as a white powder (21 mg, 29%). 1H NMR (DMSO-d6) δ 8.98 (brs, 1H), 8.61 (brs, 1H), 7.55 (m, 3H), 7.37 (m, 5H), 7.22 (m, 1H), 6.91 (s, 1H), 3.96 (brs, 2H), 1.99 (brs, 3H, water). HPLC, Rt: 3.27 min. (purity 94.5%). LC/MS, M+(ESI): 319.3, M−(ESI): 317.3.

Workup

customThe title compound was prepared following procedure
customPurification of the compound by flash chromatography on silica (EtOAc/c-Hex, 50:50)

Sources & evidence

ORD record: ord-a55720db73824257af357325b4881933
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263595B2

Reaction notes

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