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Diisopropylethylamine → HCID 57033673, compound

HRID 1250868
Notes
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Reaction equation

HRID 1250868 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:40](C(C)C)CC)(C)C.CN(C(O[N:54]1N=NC2[CH:57]=[CH:58][CH:59]=[N:60][C:55]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O1CCCC1.N1CCCN=C1N>[C:1]([O:5][C:6](=[O:7])[C@@H:8]([NH:23][S:24]([C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=1)(=[O:25])=[O:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:40][C:55]2[NH:54][CH2:57][CH2:58][CH2:59][N:60]=2)=[CH:21][CH:22]=1)([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69922482HCID 69922482, compound

Product 1

HCID 57033673HCID 57033673, compound

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineSolvent

Procedure

56 mg of 4-{4-[(2S)-2-tert-butoxycarbonyl-2-(4-trifluoromethylbenzenesulfonylamino)-ethyl]-phenoxy}-butyric acid were dissolved in tetrahydrofuran and 12.5 mg of 1,4,5,6-tetrahydropyrimidin-2-ylamine, 68 mg of diisopropylethylamine and 44 mg of HATU were added. The reaction mixture was stirred overnight, and the solvent was removed in vacuo. The residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on reversed-phase (C-18) silica gel eluting with a gradient of 10-90% acetonitrile in water. Yield 37.3 mg. MS (FAB+): m/e=613.3 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed on reversed-phase (C-18) silica gel eluting with a gradient of 10-90% acetonitrile in water

Sources & evidence

ORD record
ord-88afa19c42ee4650b8c5a96022b8b6bb
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06340679B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes