Carbodiimide → 6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(oxetan-2-ylmethyl)pyridine-2-carboxamide

HRID 385891Notes

Reaction equation

HRID 385891 reaction equation
[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][C:10]=2[F:19])[S:6][C:5]=1[NH:20][C:21]1[N:26]=[C:25]([C:27]([OH:29])=O)[CH:24]=[CH:23][CH:22]=1)=[O:3].[O:30]1[CH2:33][CH2:32][CH:31]1[CH2:34][NH2:35].O.ON1C2C=CC=CC=2N=N1.N=C=N>CN(C=O)C>[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][C:10]=2[F:19])[S:6][C:5]=1[NH:20][C:21]1[N:26]=[C:25]([C:27]([NH:35][CH2:34][CH:31]2[CH2:32][CH2:33][O:30]2)=[O:29])[CH:24]=[CH:23][CH:22]=1)=[O:3]

Participants

6

Reactant 4

HCID 160435CarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 202939311-(Oxetan-2-yl)methanamineHCID 251231676-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridine-2-carboxylic acid

Product 1

HCID 595259376-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(oxetan-2-ylmethyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridine-2-carboxylic acid (Table 3, Example 40) (50 mg, 0.12 mmol), 1-oxetan-2-ylmethanamine (11 mg, 0.12 mmol), 1-hydroxybenzotriazole hydrate (22 mg, 0.14 mmol), and PS-Carbodiimide (240 mg, 0.30 mmol, 1.25 mmol/g) in DMF (4 mL) was irradiated in a microwave at 100° C. for 10 minutes. Upon completion, the crude reaction was filtered, concentrated, and purified by silica gel chromatography (0-7% methanol/ethyl acetate) to afford the title compound.

Workup

  1. customwas irradiated in a microwave at 100° C. for 10 minutes
  2. customUpon completion, the crude reaction
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-7% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-928add3b9c154b4d95953e006a094402
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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