Sodium Hydroxide → HCID 66849728, compound

HRID 1046433Notes

Reaction equation

HRID 1046433 reaction equation
[H-].[Na+:2].C[O:4][C:5]([C:7]1[S:8][C:9]([C:29]#[C:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:10][C:11]=1[N:12]([CH:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)[C:13]([CH:15]1[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]1)=[O:14])=[O:6].F[C:36]1[CH:41]=[C:40]([CH2:42][N:43]([CH3:45])[CH3:44])[CH:39]=[CH:38][N:37]=1.[OH-].[Na+]>CN(C=O)C>[CH3:44][N:43]([CH2:42][C:40]1[CH:39]=[CH:38][N:37]=[C:36]([O:28][CH:25]2[CH2:26][CH2:27][CH:22]([N:12]([C:11]3[CH:10]=[C:9]([C:29]#[C:30][C:31]([CH3:32])([CH3:33])[CH3:34])[S:8][C:7]=3[C:5]([O-:4])=[O:6])[C:13]([CH:15]3[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]3)=[O:14])[CH2:23][CH2:24]2)[CH:41]=1)[CH3:45].[Na+:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 58113973HCID 58113973, compoundHCID 58113991HCID 58113991, compound

Product 1

HCID 66849728HCID 66849728, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (65 mg of a 60% oil dispersion, 1.62 mmol) was added to solution 5-(3,3-dimethyl-but-1-ynyl)-3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (155 mg, 0.34 mmol) and (2-fluoro-pyridin-4-ylmethyl)-dimethyl-amine (130 mg, 0.84 mmol) in DMF (4.0 mL) at 0° C. After 5 min the reaction was warmed to room temperature and then heated at 65° C. for 2 h. The reaction was cooled, aqueous NaOH (0.5 mL of a 1.0 N solution) was added and the reaction mixture evaporated to dryness. Purification by column chromatography on reverse phase C18 silica gel (100% water to 20% acetonitrile/water) provided the desired product as a colorless solid (62 mg, 31%) after lyophilization. MS (m/z): 580.2 [M+H]; HPLC retention time: 5.05 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. temperatureheated at 65° C. for 2 h
  2. temperatureThe reaction was cooled
  3. customthe reaction mixture evaporated to dryness
  4. customPurification by column chromatography on reverse phase C18 silica gel (100% water to 20% acetonitrile/water)

Sources & evidence

ORD record
ord-938cfbca17674452bc91b58c0a15ff70
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

Loading…