Ethane → HCID 46852034, compound

HRID 1262141Notes

Reaction equation

HRID 1262141 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=4)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Cl)Cl.[CH2:29]([N:31]([CH2:34]C)CC)[CH3:30].CC.[N-]=C=[O:40]>>[CH2:29]([NH:31][C:34]([NH:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([NH:18][C:15]2[N:14]=[CH:13][C:12]3=[CH:11][CH:10]=[C:9]([C:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:17]3[N:16]=2)[CH:20]=1)=[O:40])[CH3:30]

Participants

6

Reactant 5

HCID 6324EthaneHCID 6344DichloromethaneHCID 8471TriethylamineHCID 105034IsocyanateHCID 66712134HCID 66712134, compound

Product 1

HCID 46852034HCID 46852034, compound

Conditions

Temperature
0 °C

Procedure

To a solution of N-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-benzene-1,3-diamine (0.075 g, 0.22 mmol) in Methylene chloride (1.3 mL, 21 mmol) and Triethylamine (62.9 uL, 0.451 mmol) was added Ethane, isocyanato-(21.4 uL, 0.271 mmol) at 0° C. The reaction was stirred at 0° C. for 1 h. About 5% conversion. Allowed to stir at rt o/n—about 50% conversion. Heated to 50° C. for 3 hours and added additional 3.0 eq isocyanate. Reaction went to completion. Filtered off title compound as a beige ppt (34 mg, 35%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.37 (s, 1H), 8.97 (s, 1H), 89.1 (j, J=2.3 Hz, 1 h), 8.55 (dd, J=8.7 Hz, 2.5 Hz, 1H), 8.29 (s, 1 h), 7.65 (s, 1H), 7.30 (d, J=8.1 Hz, 1H), 7.20 (d, J=4.6 Hz, 1H), 7.14 (dd, J=8.2 Hz, 8.2 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 6.95 (d, J=4.8 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 6.09 t, J=5.4 Hz, 1H) 3.92 (s, 3H), 3.09 (m, 2H), 1.04 (t, J=8.14 Hz, 3H). HPLC purity=90%, rt=2.029 min, LCMS=403.9 (M+H).

Workup

  1. stirringto stir at rt o/n—about 50% conversion
  2. temperatureHeated to 50° C. for 3 hours
  3. customReaction
  4. filtrationFiltered off title compound as a beige ppt (34 mg, 35%)
  5. customHPLC purity=90%, rt=2.029 min, LCMS=403.9 (M+H)

Sources & evidence

ORD record
ord-1858587a7f5b4a2e9b740c462cccfc50
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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