HCID 68195380, compound → HCID 68195242, compound

HRID 2370644Notes

Reaction equation

HRID 2370644 reaction equation
CS([C:4]1[N:5]=[CH:6][C:7]2[C:8](=[O:27])[N:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]=[CH2:26])=[CH:19][CH:18]=3)[C:10]3[N:11]([CH:14]=[CH:15][N:16]=3)[C:12]=2[N:13]=1)=O.[NH2:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]3([CH2:47][CH2:46]3)[CH2:34][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36]2)=[CH:31][CH:30]=1>C(#N)C.C(OCC)(=O)C>[O:27]=[C:8]1[C:7]2[CH:6]=[N:5][C:4]([NH:28][C:29]3[CH:38]=[C:37]4[C:32]([C:33]5([CH2:46][CH2:47]5)[CH2:34][N:35]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:36]4)=[CH:31][CH:30]=3)=[N:13][C:12]=2[N:11]2[CH:14]=[CH:15][N:16]=[C:10]2[N:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]=[CH2:26])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 68195380HCID 68195380, compoundHCID 68195399HCID 68195399, compound

Product 1

HCID 68195242HCID 68195242, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 205E (125 mg, 0.328 mmol) in 4 mL acetonitrile was added tert-butyl 7′-amino-1′H-spiro[cyclopropane-1,4′-isoquinoline]-2′(3′H)-carboxylate (108 mg, 0.393 mmol). The reaction was heated to 60° C. overnight, cooled, diluted with ethyl acetate, washed with saturated aqueous NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified by chromatography with an Analogix 280 with an SF 24-40 column, 20% to 100% ethyl acetate/hexane gradient over 30 minutes to provide the title compound. MS (ESI+) m/z 592.36 (M+H)+.

Workup

  1. temperaturecooled
  2. washwashed with saturated aqueous NaHCO3, water, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography with an Analogix 280 with an SF 24-40 column, 20% to 100% ethyl acetate/hexane gradient over 30 minutes

Sources & evidence

ORD record
ord-d3709452e2994054a4bdae05fe747076
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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