2-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester → 2-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo [b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic Acid (2-hydroxy-ethyl)-amide

HRID 1062251Notes

Reaction equation

HRID 1062251 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH2:18][C:19](=[O:35])[NH:20][C:21]4[CH:27]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[S:9][CH:10]=1)=[O:5])C>NCCO>[OH:5][CH2:4][CH2:6][NH:7][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH2:18][C:19](=[O:35])[NH:20][C:21]4[CH:27]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[S:9][CH:10]=1)=[O:5]

Participants

3

Reactant 1

HCID 695928182-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 700018622-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo [b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic Acid (2-hydroxy-ethyl)-amideYield 83.9%

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Procedure

A solution of 2-{3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester (Example 153) (49 mg, 0.1 mmol) in 2-amino-ethanol was heated to 40° C. for 40 min. The cooled solution was partitioned between ethyl acetate and H2O and the organic layer was dried over Na2SO4 and evaporated in vacuum. The residue was triturated with ethyl acetate to give to give the title compound as light yellow solid (21 mg).

Workup

  1. customThe cooled solution was partitioned between ethyl acetate and H2O
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customevaporated in vacuum
  4. customThe residue was triturated with ethyl acetate
  5. customto give

Sources & evidence

ORD record
ord-4e6973abf3a4455cb9d016bc897a85f3
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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