Hydrochloric Acid → HCID 11211312, compound

HRID 28581Notes

Reaction equation

HRID 28581 reaction equation
[Na+].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:27][CH2:28][CH3:29])=[C:7]([C:9]2[N:14]=[C:13]([NH:15][CH3:16])[N:12]=[C:11]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([O-])=[O:23])=[CH:20][CH:19]=3)[CH:10]=2)[CH:8]=1.[Al].[Li].CO.Cl>O1CCCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:27][CH2:28][CH3:29])=[C:7]([C:9]2[N:14]=[C:13]([NH:15][CH3:16])[N:12]=[C:11]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=3)[CH:10]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 16211445Aluminum;lithiumHCID 68987729HCID 68987729, compound

Product 1

HCID 11211312HCID 11211312, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-[6-(5-chloro-2-ethoxy-phenyl)-2-methylamino-pyrimidin-4-ylamino]-benzoic acid sodium salt (100 mg, 0.25 mmol) in tetrahydofuran (20 ml) was added lithium aluminum hydide (100 mg, 2.63 mmol) in 10 portions at room temperature. After stirring for 1 hour, methanol (5 ml) was carefully added followed by hydrochloric acid (1 M, 10 ml). After stirring for 10 minutes, the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was treated with methanol (5 ml) and a solution of sodium carbonate (5.0 g) in water (15 ml). The mixture was concentrated under reduced pressure to remove methanol. Filtration and drying of the solid under reduced pressure for 12 hours yielded the title compound (80 mg, 83% yield). 1H NMR (DMSO-d6) δ 1.39 (t, 3H, J=6.93 Hz, CH3), 2.86 (d, 3H, J=4.7 Hz, OH), 4.13 (q, 2H, J=7.0 Hz, CH2), 4.45 (d, 2H, J=5.7 Hz, CH2), 5.07 (t, 1H, J=5.7 Hz, CH2), 6.75 (br s, 2H, Ar), 7.14 (d, 1H, J=8.9 Hz, Ar), 7.24 (d, 2H, J=8.5 Hz, Ar), 7.40 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.67 (d, 2H, J=8.3 Hz, Ar), 7.93 (s, 1H, NH), 9.17 (s, 1H, NH).

Workup

  1. stirringAfter stirring for 10 minutes
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthe residue was treated with methanol (5 ml)
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customto remove methanol
  7. filtrationFiltration
  8. customdrying of the solid under reduced pressure for 12 hours

Sources & evidence

ORD record
ord-0afcece23ac841a3bb1fb1cb36a792d4
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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