Ethanolamine → HCID 9946554, compound

HRID 984056Notes

Reaction equation

HRID 984056 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([OH:21])=O)[N:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:24]([CH2:26][NH2:27])[OH:25].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C>[OH:25][CH2:24][CH2:26][NH:27][C:19]([C:15]1[N:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=3)=[CH:12][CH:11]=2)[CH:18]=[CH:17][N:16]=1)=[O:21]

Participants

8

Reactant 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9879709HCID 9879709, compound

Product 1

HCID 9946554HCID 9946554, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-[4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxylic acid (1.03 g, 3.1 mmol), ethanolamine (0.31 mL, 5.08 mmol), and 1-hydroxybenzotriazol hydrate (0.53 g, 3.46 mmol) in DMF (20 mL) under nitrogen at 0° C. was added 4-methylmorpholine (0.76 mL, 6.9 mmol), and 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.68 g, 3.48 mmol). The mixture was allowed to warm to room temperature overnight. The reaction was diluted with ethyl acetate, washed 3 times with water, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give the desired product as an oil. 1H NMR (CDCl3): δ 8.82 (d, J=5.7 Hz, 1H), 8.50 (bs, 1H), 8.10 (d, J=8.7 Hz, 2H), 7.71 (d, J=5.1 Hz, 1H), 7.08-7.03 (m, 6H), 3.88 (t, J=4.2 Hz, 2H), 3.70 (q, J=4.8 Hz, 2H), 3.25 (bs, 1H).

Workup

  1. washwashed 3 times with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1cd2e568df614486bc44b2b48a8a03b4
Source dataset
uspto-grants-2005_03
Patent number
US06867210B2

Reaction notes

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