Triethylamine → HCID 90412880, compound

HRID 1522012Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=4)=[C:16]([C:17]#[N:18])[C:9]=23)[CH:7]=1.C(N(CC)CC)C.Cl[CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>CN(C)C=O>[C:17]([C:16]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][C:8]=2[C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])[NH:14][C:15]=1[C:19]1[CH2:20][CH2:21][N:22]([CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:23][CH:24]=1)#[N:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of Example 248E (125 mg, 0.359 mmol) in N,N-dimethylformamide (6 mL) was added triethylamine (0.30 mL, 2.153 mmol) and 2-chloro-N,N-dimethylacetamide (56 mg, 0.466 mmol) and the mixture was heated at 70° C. for 3 hours. After cooling, the mixture was partitioned between ethyl acetate and sodium bicarbonate and the organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (5-20% methanol in 2:1 ethyl acetate/hexane) to provide the title compound. 1H NMR (400 MHz, DMSO-d6): δ 2.77-2.80 (m, 2H), 2.86 (t, J=5.65 Hz, 2H), 2.95 (s, 3H), 3.11 (s, 3H), 3.37 (q, J=2.75 Hz, 2H), 3.77 (s, 3H), 6.65-6.67 (m, 1H), 7.04-7.12 (m, 3H), 7.15-7.21 (m, 1H), 8.34 (d, J=4.88 Hz, 1H). MS (DCI/NH3) m/z 434 (M+H)+.

Workup

temperatureAfter cooling
customthe mixture was partitioned between ethyl acetate and sodium bicarbonate
washthe organic phase was washed with brine
concentrationconcentrated
customThe residue was purified by flash chromatography (5-20% methanol in 2:1 ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b2579f7abd754cd584b5d3e8bc2b664c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073922B2

Reaction notes

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