Hydrochloric Acid → HCID 66712301, compound

HRID 1262098Notes

Reaction equation

HRID 1262098 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([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.[CH3:60][C:61]1[O:62][C:63]2[CH:69]=[CH:68][C:67]([NH2:70])=[CH:66][C:64]=2[N:65]=1.Cl>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:70][C:67]4[CH:68]=[CH:69][C:63]5[O:62][C:61]([CH3:60])=[N:65][C:64]=5[CH:66]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:7])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 7379202-Methyl-1,3-benzoxazol-5-amineHCID 178449976HCID 178449976, compound

Product 1

HCID 66712301HCID 66712301, compoundYield 40%

Procedure

Prepare mixture of N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (75 mg, 0.22 mmol), N-Phenylbis(trifluoromethanesulphonimide) (77 mg, 0.22 mmol), N,N-Diisopropylethylamine (0.113 mL, 0.650 mmol), and N,N-Dimethylformamide (2.0 mL, 26 mmol) and stir at room temperature for half an hour. Add 2-Methyl-benzoxazol-5-ylamine; hydrochloride (52 mg, 0.28 mmol) and stir at 80° C. overnight. The reaction was concentrated, dissolved in 2 mL DMSO, filtered and placed onto the Gilson. The most pure fractions were combined basified with sat. sodium bicarbonate, extracted with DCM, dried filtered, and concentrated to give N-tert-Butyl-3-[2-(2-methyl-benzoxazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide as a yellow solid (40 mg, 40%). MP=212-214° C. LCMS (E/I+) 477 (M+H). NMR 1H (DMSO-d6)-9.64 (s, 1H), 9.06 (s, 1H), 8.55 (d, 1H, J=8.20 Hz), 8.47 (s, 1H), 8.00 (s, 1H), 7.86 (d, 1H, J=8.06 Hz), 7.68-7.85 (m, 3H), 7.60 (d, 1H, J=8.86 Hz), 7.23 (d, 1H, J=4.86 Hz), 7.01 (d, 1H, J=4.86 Hz), 2.60 (s, 3H), 1.12 (s, 9H).

Workup

  1. customPrepare
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in 2 mL DMSO
  4. filtrationfiltered
  5. extractionextracted with DCM
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2dfe6d0d65a24c5988fafdae94a027d1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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