Diisopropylethylamine → HCID 57276081, compound

HRID 1250865Notes

Reaction equation

HRID 1250865 reaction equation
[C:1]1([S:7]([NH:10][C@H:11]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:12][C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])=[CH:15][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:36](C(C)C)CC)(C)C.CN(C(O[N:50]1N=NC2[CH:53]=[CH:54][CH:55]=[N:56][C:51]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O1CCCC1.N1CCCN=C1N>[C:29]([O:28][C:26](=[O:27])[C@@H:11]([NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH2:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21](=[O:22])[NH:36][C:51]2[NH:50][CH2:53][CH2:54][CH2:55][N:56]=2)=[CH:15][CH:14]=1)([CH3:31])([CH3:30])[CH3:32]

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 57041896HCID 57041896, compound

Product 1

HCID 57276081HCID 57276081, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineSolvent

Procedure

88 mg of 4-[4-((2S)-2-benzenesulfonylamino-2-tert-butoxycarbonyl-ethyl)-phenoxy]-butyric acid were dissolved in tetrahydrofuran and 22.6 mg of 1,4,5,6-tetrahydropyrimidin-2-ylamine, 123 mg of diisopropylethylamine and 79.4 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-1 8) silica gel eluting with a gradient of 10-90% acetonitrile in water. Yield 40.1 mg. MS (FAB+): m/e=545.3 (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-1 8) silica gel eluting with a gradient of 10-90% acetonitrile in water

Sources & evidence

ORD record
ord-90f4e60d88af4e47851ef3ccb2fb27f0
Source dataset
uspto-grants-2002_01
Patent number
US06340679B1

Reaction notes

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