Dimethylformamide → HCID 178500494, compound

HRID 1947270Notes

Reaction equation

HRID 1947270 reaction equation
[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)[N:11]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:10](=[O:33])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:34]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:15]2[CH2:16][CH2:17][C:12]3([N:11]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:10](=[O:33])[N:9]=[C:8]3[NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:13][CH2:14]2)=[CH:20][CH:21]=1)#[N:35]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178500496HCID 178500496, compound

Product 1

HCID 178500494HCID 178500494, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-[4-(cyclohexylamino)-8-(4-iodobenzyl)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-en-1-yl]butanoate (Intermediate I.3.a.1, 150 mg, 0.29 mmol), zinc cyanide (24 mg, 0.20 mmol) in DMF (3 mL) was added tetrakis (33 mg, 0.03 mmol). The resulting solution was allowed to stir at 80° C. for 16 h. After 16 h, the reaction mixture was filtered, concentrated in vacuo and purified by reverse phase preparative HPLC (5- 95% MeCN/H2O containing 0.1% TFA, C18) to provide the desired product. LRMS (M+1)=466.6.

Workup

  1. waitAfter 16 h
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. custompurified by reverse phase preparative HPLC (5- 95% MeCN/H2O containing 0.1% TFA, C18)

Sources & evidence

ORD record
ord-2a94164ca62245e6ad170b54a9344d86
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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