Dimethylformamide → HCID 59367666, compound

HRID 2079827Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH:13]1[CH:18]2[CH:14]1[CH2:15][N:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[CH2:17]2.CCN=C=N[CH2:33][CH2:34][CH2:35]N(C)C.Cl.C1C=CC2[N:48]([OH:49])N=NC=2C=1.CCN([CH2:55][CH3:56])CC.CN([CH:60]=[O:61])C>O>[CH2:60]([O:61][CH:55]([O:49][NH:48][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([N:16]2[CH2:15][CH:14]3[CH:18]([CH:13]3[NH:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH2:17]2)=[CH:27][CH:26]=1)[CH3:56])[CH:34]([CH3:33])[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

4-{6-[(Naphthalen-2-ylmethyl)-amino]-3-aza-bicyclo[3.1.0]hex-3-yl}-benzoic acid trimethylsylanoate (1.29 mmol) was stirred in DMF (30 ml) at r.t. under N2. EDCl (297 mg, 1.55 mmol), HOBt (209 mg, 1.55 ml), intermediate D (89 μl, 6.45 mmol) and NEt3 (899 μl, 6.45 mmol) were added and the reaction stirred at 50° C. for 24 h. After this time the reaction was cooled to r.t. and diluted with water (100 ml). It was then extracted with DCM (2×100 ml), the organic layer dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (10% MeOH in DCM) to give the title compound as an orange oil (117 mg, 19%). LCMS purity 70%, m/z 474 [M+H]+.

Workup

temperatureAfter this time the reaction was cooled to r.t.
extractionIt was then extracted with DCM (2×100 ml)
dry with materialthe organic layer dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (10% MeOH in DCM)

Sources & evidence

ORD record: ord-427850282cb24653ae4d52e042065482
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932246B2

Reaction notes

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