Hydrochloric Acid → HCID 42605945, compound

HRID 1255444Notes

Reaction equation

HRID 1255444 reaction equation
Cl.Cl[C:3]1[N:12]=[CH:11][C:10]2[N:9]3[CH:13]=[N:14][N:15]=[C:8]3[C@@H:7]([CH2:16][CH3:17])[N:6]([C@@H:18]3[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19]3)[C:5]=2[N:4]=1.[NH2:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:28][C:27]=1[O:37][CH3:38]>C(O)C.O>[F:23][C:20]1([F:24])[CH2:21][CH2:22][C@@H:18]([N:6]2[C:5]3[N:4]=[C:3]([NH:25][C:26]4[CH:36]=[CH:35][C:29]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:28][C:27]=4[O:37][CH3:38])[N:12]=[CH:11][C:10]=3[N:9]3[CH:13]=[N:14][N:15]=[C:8]3[C@H:7]2[CH2:16][CH3:17])[CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 63358506HCID 63358506, compoundHCID 86658723HCID 86658723, compound

Product 1

HCID 42605945HCID 42605945, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Concentrated hydrochloric acid (36 □l) was added to a mixture of (R)-7-chloro-5-((R)-3,3-difluorocyclopentyl)-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine (70 mg, 0.21 mmol) and 4-amino-N-ethyl-3-methoxybenzamide (59.84 mg, 0.31 mmol) in ethanol (0.9 mL) and water (3.6 mL). The reaction mixture was heated to 95° C. and stirred for 18 hours. The reaction mixture was concentrated in vacuo. The residue was taken up with ethyl acetate, washed with an aqueous saturated solution of sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the desired compound as a white solid (82 mg, 80% yield).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with an aqueous saturated solution of sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-6d0964edd5a446e7a3fa5ae0efc52c1d
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

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