Dimethylformamide → HCID 58529651, compound

HRID 1973031Notes

Reaction equation

HRID 1973031 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][N:34]([CH:36]=[O:37])C.[C:38](#N)C>>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:32][CH2:31][CH2:30][N:29]([C:36]5[O:37][CH2:38][CH2:33][N:34]=5)[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 58529733HCID 58529733, compound

Product 1

HCID 58529651HCID 58529651, compound

Procedure

5-(2-Benzyl-2H-indazol-6-yl)-7-piperidin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine (63 mg, 0.15 mmol) was dissolved in 1 mL of acetonitrile and 0.5 ml. DMF and treated with 2-bromoethyl isocyante (0.013 mL, 0.16 mmol) and the mixture was stirred 3 h. The reaction was quenched by the addition of −0.2 mL water. This mixture was directly injected on to a preparative HPLC. The product containing fractions were collected, and the TFA from the eluate was removed via filtration through an acidic resin followed by washing with acetonitrile. The product was then eluted with 2M NH3 in MeOH. The MeOH was removed and the residue was dried overnight in a vacuum oven at 40° C. to provide the title compound. NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.91 (s, 1H), 7.80 (d, 1H), 7.59 (s, 4H), 7.38-7.24 (m, 5H), 7.12 (d, 1H), 6.61 (s, 1H), 5.62 (s, 2H), 4.24 (m, 2H), 4.10 (dd, 1H), 3.83 (dd, 1H), 3.61 (m, 2H), 2.93 (m, 1H), 2.89 (m, 1H), 2.08 (m, 1H) 1.72 (m, 2H), 1.58 (m, 1H). ES-MS m/z 493.2 [M+H]+, HPLC RT (min) 2.29.

Workup

  1. customThe reaction was quenched by the addition of −0.2 mL water
  2. additionThe product containing fractions
  3. customwere collected
  4. customthe TFA from the eluate was removed via filtration through an acidic resin
  5. washby washing with acetonitrile
  6. washThe product was then eluted with 2M NH3 in MeOH
  7. customThe MeOH was removed
  8. customthe residue was dried overnight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-3265890180714ca8abe8a1d4c0b5903a
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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