Diisopropylethylamine → HCID 57070053, compound

HRID 1250860Notes

Reaction equation

HRID 1250860 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([NH:23][S:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[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.F[P-](F)(F)(F)(F)F.[N:53]1(OC(N(C)C)=[N+](C)C)[C:57]2[N:58]=[CH:59][CH:60]=[CH:61]C=2N=N1>O1CCCC1.N1CCCN=C1N>[C:1]([O:5][C:6](=[O:7])[C@@H:8]([NH:23][S:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:25])=[O:26])[CH2:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:40][C:57]2[NH:53][CH2:61][CH2:60][CH2:59][N:58]=2)=[CH:12][CH:11]=1)([CH3:3])([CH3:2])[CH3:4]

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 69920335HCID 69920335, compound

Product 1

HCID 57070053HCID 57070053, compound

Reagents, catalysts & solvents 2

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

Procedure

61 mg of 4-{4-[(2S)-2-tert-butoxycarbonyl-2-(naphthalene-1-sulfonylamino)-ethyl]-phenoxy}-butyric acid were dissolved in tetrahydrofuran and 14 mg of 1,4,5,6-tetrahydropyrimidin-2-ylamine, 0.103 ml of diisopropylethylamine and 49.7 mg of 7-azabenzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (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 31 mg. MS (FAB+): m/e=595.3 (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-69c975db3da74a719567850176d2e651
Source dataset
uspto-grants-2002_01
Patent number
US06340679B1

Reaction notes

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