Dimethylformamide → HCID 66711098, compound

HRID 1262094Notes

Reaction equation

HRID 1262094 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17](O)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[NH2:56][C:57]1[CH:62]=[CH:61][C:60]([CH:63]2[CH2:68][CH2:67][N:66]([CH2:69][C:70]([NH2:72])=[O:71])[CH2:65][CH2:64]2)=[CH:59][CH:58]=1>>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([NH:56][C:57]4[CH:62]=[CH:61][C:60]([CH:63]5[CH2:64][CH2:65][N:66]([CH2:69][C:70]([NH2:72])=[O:71])[CH2:67][CH2:68]5)=[CH:59][CH:58]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 574161072-[4-(4-Aminophenyl)piperidin-1-yl]acetamideHCID 178458337HCID 178458337, compound

Product 1

HCID 66711098HCID 66711098, compound

Procedure

7-(3-Isopropoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (100 mg, 0.4 mmol), N-Phenylbis(trifluoromethanesulphonimide) (146 mg, 0.408 mmol), N,N-Diisopropylethylamine (0.194 mL, 1.11 mmol), and N,N-Dimethylformamide (3 mL, 40 mmol) and stir at room temperature for half an hour. Add 2-[4-(4-Amino-phenyl)-piperidin-1-yl]-acetamide (139 mg, 0.594 mmol) and stir at 60° C. overnight. The reaction was concentrated, DMSO added, filtered and placed onto the Gilson for purification. The most pure fractions were basified with saturated sodium bicarbonate, extracted with ethyl acetate, dried, filtered and collected as a yellow solid (47 mg, 30%). MP 233-235° C. LCMS (E/I+) 485 (M+H). NMR 1H (DMSO-d6)-9.43 (s, 1H), 8.97 (s, 1H), 7.82 (s, 1H), 7.73 (d, 2H, J=8.04 Hz), 7.66 (d, 1H, J=7.72 Hz), 7.43 (t, 1H, J=7.80 Hz), 7.14-7.22 (m, 5H), 6.98 (d, 1H, J=8.17 Hz), 6.94 (d, 1H, J=4.50 Hz), 4.70-4.75 (m, 1H), 2.87-2.95 (m, 4H), 2.40-2.46 (m, 1H), 2.10-2.22 (m, 2H), 1.70-1.76 (m, 4H), 1.31 (d, 6H, J=5.79 Hz).

Workup

  1. concentrationThe reaction was concentrated
  2. additionDMSO added
  3. filtrationfiltered
  4. customplaced onto the Gilson for purification
  5. extractionextracted with ethyl acetate
  6. customdried
  7. filtrationfiltered
  8. customcollected as a yellow solid (47 mg, 30%)

Sources & evidence

ORD record
ord-3fca0fe86f9340f3b20f343fd9ecbc0b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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