Acetyl chloride → HCID 21864953, compound

HRID 131172Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:17][C:4]=2[O:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])=[O:8].[C:25](Cl)(=[O:27])[CH3:26].[C:29](OCC)(=[O:31])[CH3:30].CCCCCC>ClC(Cl)C>[C:25]([N:1]([C:2]1[C:3]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:17][C:4]=2[O:5][C:6]=1[C:7](=[O:8])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])[C:29](=[O:31])[CH3:30])(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (3-amino-5,6,7,8-tetrahydronaphtho[2,3-b]furan-2-yl)(2,4-dichlorophenyl)methanone (150 mg, 0.46 mmol) from Example 142, acetyl chloride (0.16 mL, 2.3 mmol, 5.0 eq), and diisopropylethylamine polystyrene resin (245 mg, 0.92 mmol, 2.0 eq, 3.77 mol/g loading) in dichloroethane (4.6 mL) was shaken at 70° C. for 15 h. The resin was filtered and washed with dichloromethane (2×10 mL), methanol (2×10 mL), and dichloromethane (2×10 mL). The filtrate was evaporated in vacuo. Crystallization from ether-hexane gave 73.2 mg (35.8%) as a white solid. 1H-NMR (DMSO-d6) δ 7.82 (s, 1H), 7.62 (d, J=0.6 Hz, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.46 (broad s, 2H), 2.84 (m, 4H), 2.20 (s, 6H), 1.73 (broad s, 4H); MS GC-MS (MH+=444/445); Rf=0.55 (25% ethyl acetate-hexane).

Workup

filtrationThe resin was filtered
washwashed with dichloromethane (2×10 mL), methanol (2×10 mL), and dichloromethane (2×10 mL)
customThe filtrate was evaporated in vacuo
customCrystallization from ether-hexane
customgave 73.2 mg (35.8%) as a white solid

Sources & evidence

ORD record: ord-6faa40763e02403bb25b96e31d2756fc
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384947B2

Reaction notes

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