Ammonia → HCID 86732357, compound

HRID 517236Notes

Reaction equation

HRID 517236 reaction equation
F[B-](F)(F)F.C[N+:7](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[C:49]3[C:48](=[O:50])[CH2:47][CH:46]([C:51]([OH:53])=O)[CH2:45][C:44]=3[N:43]([C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([C:60]([F:63])([F:62])[F:61])[CH:55]=3)[C:42](=[O:64])[NH:41]2)=[CH:36][CH:35]=1)#[N:33].N>CN(C)C=O.O>[C:32]([C:34]1[CH:35]=[CH:36][C:37]([CH:40]2[C:49]3[C:48](=[O:50])[CH2:47][CH:46]([C:51]([NH2:7])=[O:53])[CH2:45][C:44]=3[N:43]([C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([C:60]([F:63])([F:62])[F:61])[CH:55]=3)[C:42](=[O:64])[NH:41]2)=[CH:38][CH:39]=1)#[N:33]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86732358HCID 86732358, compound

Product 1

HCID 86732357HCID 86732357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (50 mg, 0.16 mmol) and N,N-diisopropylethylamine (60 μL, 0.34 mmol) are added to a solution of 4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquina zoline-7-carboxylic acid (example 10, 70 mg, 0.154 mmol) in N,N-dimethylformamide (1.0 mL). After 10 min aqueous ammonia (35%, 0.5 mL) is added and the mixture is stirred at room temperature for 1 h. Water is added and the mixture is extracted with diethyl ether. The organic layer is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of methanol in water, 0.1% TFA). Yield: 15 mg; ESI mass spectrum [M+H]+=455; Retention time HPLC: 1.02 min (V001—006).

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of methanol in water, 0.1% TFA)
  4. custom1.02 min (V001—006)

Sources & evidence

ORD record
ord-b1e90005a1b845919e28136745a082f6
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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