HCID 178452634, compound → HCID 178512234, compound

HRID 1971211Notes

Reaction equation

HRID 1971211 reaction equation
[C:1]([N:3]=[C:4]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][CH:13]([NH:16]C(OC(C)(C)C)=O)[CH2:12][CH2:11][C:10]=2[CH:24]=1)#[N:2]>C(O)(C)C.[H][H].[Pd]>[C:1]([N:3]=[C:4]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12][CH2:11][C:10]=2[CH:24]=1)#[N:2]

Participants

4

Reactant 1

HCID 178452634HCID 178452634, compound

Product 1

HCID 178512234HCID 178512234, compound

Reagents, catalysts & solvents 2

HCID 178506449HCID 178506449, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

The single enantiomer was then BOC-protected, the nitro group reduced by treatment with H2/Pd and the primary aniline treated with diphenyl cyanocarboimidate (slight excess) in 20 mL of isopropanol with stirring at ambient temperature overnight. The solid was filtered, washed with isopropanol and ether and dried to give phenyl (7S)-N′-cyano-N-(7-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2-yl)carbamimidate, as a white solid in high yield (from the single enantiomer via transamination).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with isopropanol and ether
  3. customdried

Sources & evidence

ORD record
ord-a03d212fd26343c08d324d411c211fb2
Source dataset
uspto-grants-2013_04
Patent number
US08431594B2

Reaction notes

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