Ethanolamine → HCID 58851269, compound

HRID 1696606Notes

Reaction equation

HRID 1696606 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:12])[N:7]([C:24]2[CH:25]=[C:26]([CH2:30][C:31](O)=[O:32])[CH:27]=[CH:28][CH:29]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:34][CH2:35][CH2:36][OH:37].CCN(CC)CC>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:12])[N:7]([C:24]2[CH:25]=[C:26]([CH2:30][C:31]([NH:34][CH2:35][CH2:36][OH:37])=[O:32])[CH:27]=[CH:28][CH:29]=2)[N:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 67271988HCID 67271988, compound

Product 1

HCID 58851269HCID 58851269, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(3-(3-t-butyl-5-(3-(naphthalen-1-yl)ureido)-1H-pyrazol-1-yl)phenyl)acetic acid (200 mg, 0.43 mmol) in THF (10 mL) was added 2-amino-ethanol (260 mg, 4.3 mmol) and Et3N (0.5 mL), then this mixture was heated to 40° C. and stirred overnight. After removal of the solvent, this mixture was extracted with EtOAc and washed with 1N HCl aqueous solution and the organic layer was dried over Na2SO4. After removal of the solvent, a crude product was obtained, which was purified by preparative HPLC to afford 2-{3-[3-t-butyl-5-(3-naphthalen-1-yl-ureido)pyrazol-1-yl]phenyl}-N-(2-hydroxy-ethyl)acetamide (104 mg, 50% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.01 (s, 1H), 8.81 (s, 1H), 8.12 (m, 1H), 7.98 (d, J=9.3 Hz, 1H), 7.92-7.87 (m, 2H), 7.61 (d, J=8.1 Hz, 1H), 7.53-7.49 (m, 2H), 7.47-7.38 (m, 4H), 7.29 (d, J=7.5 Hz, 1H), 6.39 (s, 1H), 3.49 (s, 2H), 3.35 (t, J=6.0 Hz, 2H), 3.07 (q, J=6.0 Hz, 2H), 1.25 (s, 9H); MS (ESI) m/z: 487 (M+H+).

Workup

  1. customAfter removal of the solvent
  2. extractionthis mixture was extracted with EtOAc
  3. washwashed with 1N HCl aqueous solution
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customAfter removal of the solvent
  6. customa crude product was obtained
  7. customwhich was purified by preparative HPLC

Sources & evidence

ORD record
ord-ba9587ec0e0241b18dfb4f63f5aa1bb2
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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