Lawesson's reagent → HCID 59513778, compound

HRID 1159880Notes

Reaction equation

HRID 1159880 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[N:17]=[C:16]([C:18]4[C:19]([C:27]5[CH:28]=[C:29]([NH:33][C:34](=O)[C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[CH:30]=[CH:31][CH:32]=5)=[N:20][N:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=45)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[N:17]=[C:16]([C:18]4[C:19]([C:27]5[CH:28]=[C:29]([NH:33][C:34](=[S:51])[C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[CH:30]=[CH:31][CH:32]=5)=[N:20][N:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=45)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59513724HCID 59513724, compound

Product 1

HCID 59513778HCID 59513778, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(3-{3-[2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-pyrimidin-4-yl]-pyrazolo[1,5-a]pyridin-2-yl}-phenyl)-benzamide (43 mg, 0.08 mmol) and excess of Lawesson's Reagent in 1,4-dioxane (1 mL) was heated at 100° C. in a sealed tube. When LC/MS showed the starting material to be consumed, the mixture was cooled to ambient temperature and diluted with DCM. The organic phase was washed with water, dried over MgSO4 and concentrated. The crude material was purified through silica gel to give the title compound as a yellow solid. 1H NMR (400 MHz, d6-DMSO): δ 11.85 (s, 1H), 9.34 (s, 1H), 8.82 (d, J=6.8 Hz, 1H), 8.49 (d, J=8.4 Hz, 1H), 8.20 (d, J=5.6 Hz, 1H), 8.14 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H), 7.57-7.42 (m, 6H), 7.35 (m, 1H), 7.13-7.10 (m, 2H), 6.73 (d, J=8.8 Hz, 1H), 6.49 (d, J=5.2 Hz, 1H), 4.19 (m, 4H). MS (ESI) m/z=557 [M+H]+.

Workup

  1. customto be consumed
  2. additiondiluted with DCM
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified through silica gel

Sources & evidence

ORD record
ord-944f376c001948d8a7f6f0891b2a9d42
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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