Hydrochloric Acid → HCID 178427365, compound

HRID 80813Notes

Reaction equation

HRID 80813 reaction equation
[CH:1]([C:4]1[CH:8]=[C:7]([N:9]2[CH2:40][CH2:39][C:12]3[N:13]=[C:14]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]5[C:20]=4[C:21]([CH3:38])=[CH:22][N:23]5[S:28]([C:31]4[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[N:15]=[C:16]([O:17]C)[C:11]=3[CH2:10]2)[N:6]([CH3:41])[N:5]=1)([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>C(O)C>[CH:1]([C:4]1[CH:8]=[C:7]([N:9]2[CH2:40][CH2:39][C:12]3[N:13]=[C:14]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]5[C:20]=4[C:21]([CH3:38])=[CH:22][N:23]5[S:28]([C:31]4[CH:32]=[CH:33][C:34]([CH3:35])=[CH:36][CH:37]=4)(=[O:30])=[O:29])[N:15]=[C:16]([OH:17])[C:11]=3[CH2:10]2)[N:6]([CH3:41])[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 712405966-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 178427365HCID 178427365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.8 g, 3.15 mmol), prepared as described in Example 16, in ethanol (10 mL) in a 150 mL sealed tube, was added concentrated hydrochloride (10 mL). After the tube was sealed, the reaction was stirred and heated to 85° C. for 18 h. The reaction mixture wascooled to 0° C. and poured into ice water. Solid NaHCO3 was added to neutralize the reaction mixture, then the mixture was extracted with DCM twice and the combined organic layers were dried over Na2SO4. The resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane) to provide 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol. MS (ESI+) m/z 557.2 (M+H)+.

Workup

  1. customsealed tube
  2. customAfter the tube was sealed
  3. customwascooled to 0° C.
  4. extractionthe mixture was extracted with DCM twice
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customThe resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-96b099b45a6a46609632f4e8338c22f1
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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