Formamide → (1S)-1-(1-{[2-cyano-4-(1,3-thiazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422545Notes

Reaction equation

HRID 2422545 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]([NH2:17])=O.[N+:18]([C:21]1[CH:58]=[CH:57][C:24]([C:25]([O:27][C@@:28]([C:35]2[N:36]=[N:37][N:38]([CH2:40][C:41]3[CH:50]=[C:49]4[C:44]([C:45]([C:53](=O)[CH2:54]Br)=[CH:46][C:47]([C:51]#[N:52])=[N:48]4)=[CH:43][CH:42]=3)[CH:39]=2)([C:31]([F:34])([F:33])[F:32])[CH2:29][CH3:30])=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>O1CCOCC1.C(OCC)(=O)C>[N+:18]([C:21]1[CH:58]=[CH:57][C:24]([C:25]([O:27][C@@:28]([C:35]2[N:36]=[N:37][N:38]([CH2:40][C:41]3[CH:50]=[C:49]4[C:44]([C:45]([C:53]5[N:17]=[CH:15][S:2][CH:54]=5)=[CH:46][C:47]([C:51]#[N:52])=[N:48]4)=[CH:43][CH:42]=3)[CH:39]=2)([C:31]([F:34])([F:33])[F:32])[CH2:29][CH3:30])=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 86621977(S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Product 1

HCID 66790904(1S)-1-(1-{[2-cyano-4-(1,3-thiazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of P4S10 (34 mg, 0.08 mmol) in dioxane (1 mL) at 0° C. was added formamide (57 mg, 1.26 mmol). The reaction mixture was warmed to room temperature for 1 h. A solution of 1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (see Example 52, Step 2) (160 mg, 0.25 mmol) in dioxane (1 mL) was then added and the mixture stirred at room temperature overnight. The reaction mixture was diluted in ethyl acetate, washed with water, brine and dried over MgSO4. The crude compound was purified on silica gel (eluting solvent: 5% acetone in dichloromethane) to give the desired product. 1H NMR (acetone-d6): δ 9.35 (s, 1H), 8.80 (d, 1H), 8.55 (s, 1H), 8.40 (m, 3H), 8.30 (d, 2H), 8.22 (s, 1H), 8.05 (s, 1H), 7.75 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.15 (t, 3H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customThe crude compound was purified on silica gel (eluting solvent: 5% acetone in dichloromethane)

Sources & evidence

ORD record
ord-3671ed42f7e14ef1b3a2a7c94000399e
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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