Ethanolamine → HCID 16222298, compound

HRID 605687Notes

Reaction equation

HRID 605687 reaction equation
[F:1][C:2]1[C:3]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=2[F:26])=[C:4]([C:9]([N:11]2[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][CH2:52][CH2:53][OH:54].CN1CCOCC1>CN(C)C=O.C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=2[F:26])=[C:4]([C:9]([N:11]2[CH2:12][CH:13]([C:15]([NH:51][CH2:52][CH2:53][OH:54])=[O:17])[CH2:14]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25027257HCID 25027257, compound

Product 1

HCID 16222298HCID 16222298, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)azetidine-3-carboxylic acid (15 mg, 0.03 mmol), prepared using procedures similar to those in Example 1, in N,N-dimethylformamide (2.00 mL) was added HBTU (38 mg, 0.10 mmol). The mixture was stirred for 15 minutes at room temperature followed by the addition of 2-aminoethanol (3.6 μL, 0.06 mmol) and N-methylmorpholine (110 μL, 1.00 mmol). The mixture was allowed to stir at room temperature for 3 d, then diluted the mixture with chloroform (20 mL), and washed with water (30 mL). The aqueous phase was back extracted with chloroform (10 mL). The combined organic phases were dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by high pressure liquid chromatography to afford the title compound (9.20 mg, 58%) as the trifluoroacetic acid salt: 1H NMR (400 MHz, CDCl3): 8.54 (s, 1H), 7.41-7.37 (m, 1H), 7.34-7.31 (m, 1H), 7.18-7.14 (m, 1H), 6.85-6.77 (m, 1H), 6.64-6.58 (m, 1H), 4.66 (br, 1H), 4.40-4.24 (br, 3H), 3.83-3.23 (br m, 7H), 1.18 (t, 3H); MS (EI) for C19H17F3IN3O3: 542 (MNa+).

Workup

  1. stirringto stir at room temperature for 3 d
  2. washwashed with water (30 mL)
  3. extractionThe aqueous phase was back extracted with chloroform (10 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-4b1a3f1c91294a0f9027c31c46fd9032
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

Loading…