Formic Acid → HCID 25142827, compound

HRID 1677039Notes

Reaction equation

HRID 1677039 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:30][CH2:29][C:20]3[NH:21][C:22]4[C:23]([OH:28])=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2].Br[CH2:32][C:33]#[N:34].C(=O)([O-])[O-].[K+].[K+].C(O)=O>CN(C=O)C.CC#N.O>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:30][CH2:29][C:20]3[NH:21][C:22]4[C:23]([O:28][CH2:32][C:33]#[N:34])=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 25142825HCID 25142825, compound

Product 1

HCID 25142827HCID 25142827, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Following Example 34 (1R,2R)-2-(6-hydroxy-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carbonyl)-cyclohexanecarboxylic acid (1-cyano-cyclopropyl)-amide (102 mg, 0.25 mmol), bromoacetonitrile (50 uL, 0.75 mmol) and potassium carbonate (104 mg, 0.75 mmol) in DMF (5 mL) were heated to 80° C. for 1 h when reaction was ca 60% complete. Preparative HPLC (0.5% HCOOH, CH3CN/H2O gradient) to give a yellow solid (51.9, 47%).

Workup

  1. customwhen reaction

Sources & evidence

ORD record
ord-c0d397f081b1430eb9163b4f8139db39
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

Loading…