Water → HCID 178522762, compound

HRID 1695682Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:22]=[CH:21][C:6]2[N:7]=[C:8]([NH:11][C@H:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH2:13]3)[O:9][CH2:10][C:5]=2[CH:4]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1.O>O1CCCC1>[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][CH2:2][C:3]2[CH:22]=[CH:21][C:6]3[N:7]=[C:8]([NH:11][C@H:12]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH2:14][CH2:13]4)[O:9][CH2:10][C:5]=3[CH:4]=2)=[O:36])=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (ice bath) and stirred solution of (6-aminomethyl-4H-benzo[d][1,3]oxazin-2-yl)-(R)-indan-1-yl-amine (example 129) (200 mg, 0.68 mmol) and triethylamine (76 mg, 0.75 mmol) in tetrahydrofuran (4 ml) was added 4-fluorobenzoyl chloride (119 mg, 0.75 mmol) and the mixture was allowed to stir at 0° C. for 1 h and afterwards at room temperature for 16 h. The reaction mixture was poured into water (15 ml) and extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with brine (20 ml), dried (magnesium sulfate) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as white foam (191 mg, 67%). MS (ISP): m/e=416.3 (M+H+).

Workup

temperatureTo a cooled (ice bath)
extractionextracted with ethyl acetate (2×20 ml)
washThe combined organic layers were washed with brine (20 ml)
dry with materialdried (magnesium sulfate)
customevaporated
customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record: ord-f348d692b3904c16878358fa672a999a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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