Ammonia → HCID 86647870, compound

HRID 389765Notes

Reaction equation

HRID 389765 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][C:23]([NH:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[N:22][C:21]=3[C:32](O)=[O:33])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)O.C([N:53](C(C)C)CC)(C)C.N.O1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:77]2N=C[CH:80]=[CH:81][C:76]=2N=N1>CN(C=O)C>[C:32]([C:21]1[N:22]=[C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[O:24][C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][CH2:77][CH2:76][CH2:81][CH3:80])=[O:7])[CH2:13][CH2:12]2)=[CH:19][CH:18]=1)(=[O:33])[NH2:53]

Participants

8

Reactant 6

HCID 222Ammonia2×HCID 312751,4-Dioxane2×HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21864398Tetramethyluronium hexafluorophosphateHCID 68561263HCID 68561263, compound

Product 1

HCID 86647870HCID 86647870, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-2-(pyridin-3-ylamino)oxazole-4-carboxylic acid (0.046 g, 0.1 mmol) in DMF (1 ml) was added O-7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.065 g, 0.17 mmol), diisopropylethylamine (0.03 ml, 0.17 mmol) and 0.5M NH3 in dioxane (0.6 ml, 0.3 mmol) and the resultant mixture stirred at room temperature overnight. A further portion of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.020 g, 0.05 mmol), diisopropylethylamine (0.01 ml, 0.056 mmol) and 0.5M NH3 in dioxane (0.2 ml, 0.1 mmol) was added and the reaction stirred for 1 hour. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford tent-butyl 4-(4-(4-carbamoyl-2-(pyridin-3-ylamino)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.006 g, 0.013 mmol, 13%). LCMS (2) Rt: 2.64 min; m/z (ES+) 465.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-4444e8167dde48db8767033618a2e812
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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