Hydrochloric Acid → HCID 58484965, compound

HRID 1255435Notes

Reaction equation

HRID 1255435 reaction equation
Cl.Cl[C:3]1[N:4]=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9][N:8]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)[C:7]=2[N:24]=1.[NH2:25][C:26]1[CH:37]=[CH:36][C:29]([C:30]([NH:32][CH:33]2[CH2:35][CH2:34]2)=[O:31])=[CH:28][C:27]=1[O:38][CH3:39]>C(O)C.O>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:36]=[CH:37][C:26]([NH:25][C:3]3[N:4]=[CH:5][C:6]4[N:12]([CH3:13])[C:11](=[O:14])[C:10]([CH3:15])([CH3:16])[CH2:9][N:8]([C@@H:17]5[CH2:21][CH2:20][C:19]([F:22])([F:23])[CH2:18]5)[C:7]=4[N:24]=3)=[C:27]([O:38][CH3:39])[CH:28]=2)[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58484976HCID 58484976, compoundHCID 67447132HCID 67447132, compound

Product 1

HCID 58484965HCID 58484965, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Concentrated hydrochloric acid (52 μl) was added to a mixture of (R)-2-chloro-9-(3,3-difluorocyclopentyl)-5,7,7-trimethyl-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (100 mg, 0.29 mmol) and 4-amino-N-cyclopropyl-3-methoxybenzamide (90 mg, 0.44 mmol) in ethanol (1.4 mL) and water (5.2 mL). The reaction mixture was heated to 85° C. and stirred for 48 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in 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 title compound as a white solid (83 mg, 56% yield).

Workup

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

Sources & evidence

ORD record
ord-64e300eee14344ea92dd356fdaf34637
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

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