Dimethylformamide → HCID 46852668, compound

HRID 1262093Notes

Reaction equation

HRID 1262093 reaction equation
[CH3:1][S:2]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20](O)=[N:21]3)=[CH:16][CH:15]=2)[CH2:6]1)(=[O:4])=[O:3].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.[NH2:59][C:60]1[CH:65]=[CH:64][C:63]([CH:66]2[CH2:69][N:68]([CH2:70][C:71]([NH2:73])=[O:72])[CH2:67]2)=[CH:62][CH:61]=1>>[CH3:1][S:2]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20]([NH:59][C:60]4[CH:65]=[CH:64][C:63]([CH:66]5[CH2:67][N:68]([CH2:70][C:71]([NH2:73])=[O:72])[CH2:69]5)=[CH:62][CH:61]=4)=[N:21]3)=[CH:16][CH:15]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 574160632-[3-(4-Aminophenyl)azetidin-1-yl]acetamideHCID 178504916HCID 178504916, compound

Product 1

HCID 46852668HCID 46852668, compoundYield 7.7%

Procedure

7-(2-Methanesulfonyl-2,3-dihydro-1H-isoindol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (80 mg, 0.2 mmol), N-Phenylbis(trifluoromethanesulphonimide) (95.1 mg, 0.266 mmol), N,N-Diisopropylethylamine (0.126 mL, 0.726 mmol), and N,N-Dimethylformamide (2 mL, 30 mmol) and stir at room temperature for half an hour. Add 2-[3-(4-Amino-phenyl)-azetidin-1-yl]-acetamide (71 mg, 0.34 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 collected, basified with sat sodium bicarbonate extracted with EtOAc, dried, filtered and concentrated to give a yellow solid (8 mg, 6%). MP 216-218° C. LCMS (E/I+) 518 (M+H). NMR 1H (DMSO-d6)-9.48 (s, 1H), 9.02 (s, 1H), 7.97 (d, 1H, J=7.81 Hz), 7.64 (d, 2H, J=8.55 Hz), 7.56 (t, 1H, J=7.80 Hz), 7.44 (d, 1H, J=7.74 Hz), 7.21 (d, 2H, J=8.34 Hz), 7.12 (bs, 1H), 7.05-7.08 (m, 2H), 6.99 (d, 1H, J=4.69 Hz), 4.74 (s, 4H), 3.69 (t, 2H, J=7.40 Hz), 3.53-3.61 (m, 1H), 3.15 (t, 2H, J=6.86 Hz), 3.02 (s, 2H), 2.92 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionDMSO added
  3. filtrationfiltered
  4. customplaced onto the Gilson for purification
  5. customThe most pure fractions were collected
  6. extractionextracted with EtOAc
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-abbc08c1f2c24e8885abddf908e8cb64
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…