Ammonia → HCID 68521339, compound

HRID 1410494Notes

Reaction equation

HRID 1410494 reaction equation
[C:1]([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]([OH:34])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:42]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.N.O1CCOCC1>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[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)=[CH:19][CH:18]=1)(=[O:34])[NH2:42]

Participants

7

Reactant 5

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)2×HCID 68561263HCID 68561263, compound

Product 1

HCID 68521339HCID 68521339, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in example R-13 with the exception that step c was performed as follows: 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 m, 0.17 mmol) and 0.5M NH3 in dioxane (0.6 m, 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 m, 0.056 mmol) and 0.5M NH3 in dioxane (0.2 m, 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 tert-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. 1H NMR (DMSO) δ 2.84 (4H, t), 3.16 (4H, t), 6.99 (2H, d), 7.35 (1H, dd), 7.44 (1H, br s), 7.66 (1H, br s), 8.07 (2H, d), 8.19 (1H, dd), 8.35 (1H, dd), 8.77 (1H, d), 10.60 (1H, br s). LCMS (2) Rt: 1.62 min; m/z (ES+) 365.

Workup

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

Sources & evidence

ORD record
ord-6eb8c3779d0240e18a6da9c0c2450677
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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