Hydrochloric Acid → HCID 59232146, compound

HRID 1099308Notes

Reaction equation

HRID 1099308 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:46])[NH:34][C:35]4[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:36]=4[F:45])=[C:28]([F:47])[CH:27]=3)[CH:9]=[C:10]([C:11]([CH:13]3[O:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.Cl>O1CCOCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:34][C:35]4[CH:40]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:38]=[CH:37][C:36]=4[F:45])=[O:46])=[C:28]([F:47])[CH:27]=3)[CH:9]=[C:10]([C:11]([CH:13]3[O:18][CH2:17][CH2:16][NH:15][CH2:14]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59232230HCID 59232230, compound

Product 1

HCID 59232146HCID 59232146, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 2-({4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]pyrrolo[2,1-f][1,2,4]triazin-7-yl}carbonyl)morpholine-4-carboxylate (50 mg, 0.076 mmol) in 1,4-dioxane (1 mL) was treated with 4N HCl (200 μL) in 1,4-dioxane and stirred at rt for 4 h. The reaction was concentrated then diluted with EtOAc and saturated NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated. The crude residue was triturated with EtOAc and filtered. A yellow solid was isolated (24 mg, 57%). 1H-NMR (CD3OD) δ 8.65 (d, J=8.2 Hz, 1 H), 8.32 (t, J=8.5 Hz, 1 H), 8.09 (s, 1 H), 7.48 (s, 1 H), 7.34-7.29 (m, 4 H), 5.26 (dd, J1=9.6 Hz, J2=2.6 Hz, 1 H), 4.65-4.60 (m, 1H), 4.00 (dt, J1=11.6 Hz, J2=2.5 Hz, 1 H), 3.82-3.75 (m, 1 H), 2.89-2.86 (m, 2 H), 2.75 (dd, J1=12.8 Hz, J2=9.6 Hz, 1 H); MS [M+H]+=562.1; LCMS RT=2.66 min.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthen diluted with EtOAc and saturated NaHCO3 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was triturated with EtOAc
  6. filtrationfiltered
  7. customA yellow solid was isolated (24 mg, 57%)

Sources & evidence

ORD record
ord-925b040bd61044e98c4176d04d504e8b
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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