Hydrochloric Acid → HCID 11383098, compound

HRID 1813982Notes

Reaction equation

HRID 1813982 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[CH:3]=1.[BH4-].[Na+].O.Cl>O1CCCC1.CO>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 11268641HCID 11268641, compound

Product 1

HCID 11383098HCID 11383098, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound provided by Example 12 (25 mg, 0.068 mmol) in tetrahydofuran (5 ml) and methanol (10 ml) was added sodium borohydride (20 mg, 0.53 mmol). After stirring for 1.5 hours, the mixture was treated with water (10 ml) and hydrochloric acid (1 M, 0.6 ml). The mixture was concentrated to a volume of 8 ml and the solid was collected by filtration. The solid was treated with aqueous sodium carbonate solution (10%, 10 ml) and extracted with ethyl acetate (3×30 ml). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with methanol-dichloromethane (5:95) to give the title compound (10 mg, 39% yield). 1H NMR (acetone-d6) δ1.36 (t, 3H, J=6.9 Hz, CH3), 3.95 (bs, 1H, OH), 4.09 (q, 2H, J=7.0 Hz, CH2), 4.56 (s, 2H, CH2), 5.28 (bs, 2H, NH2), 6.16 (d, 1H, J=1.1 Hz, Ar), 6.34 (d, 1H, J=1.1 Hz, Ar), 7.09 (d, 1H, J=8.5 Hz, Ar), 7.24 (d, 2H, J=8.8 Hz, Ar), 7.30-7.34 (m, 2H, Ar), 7.60-7.63 (m, 2H, Ar), 7.80 (s, 1H, NH).

Workup

  1. concentrationThe mixture was concentrated to a volume of 8 ml
  2. filtrationthe solid was collected by filtration
  3. additionThe solid was treated with aqueous sodium carbonate solution (10%, 10 ml)
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative thin layer chromatography
  8. washeluting with methanol-dichloromethane (5:95)

Sources & evidence

ORD record
ord-2e9fd043b245422aa5ba4b3f6a2c5f2f
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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