Tetrahydrofuran → HCID 178482395, compound

HRID 450334Notes

Reaction equation

HRID 450334 reaction equation
[CH3:1][NH:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]2)[N:4]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1COCC1.[F:52][C:53]([F:62])([F:61])[C@H:54]1[CH2:59][CH2:58][C@H:57]([NH2:60])[CH2:56][CH2:55]1>O.CN(C=O)C>[F:52][C:53]([F:61])([F:62])[C@H:54]1[CH2:55][CH2:56][C@H:57]([NH:60][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:3]([NH:2][CH3:1])=[N:4][C:5]=2[N:15]2[CH2:20][CH2:19][CH:18]([C:21]([F:23])([F:24])[F:22])[CH2:17][CH2:16]2)[CH2:58][CH2:59]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 679584096-Methylamino-5-nitro-2-(4-trifluoromethyl-piperidinyl)-nicotinic acidHCID 178511531HCID 178511531, compound

Product 1

HCID 178482395HCID 178482395, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methylamino-5-nitro-2-(4-trifluoromethyl-piperidinyl)-nicotinic acid (570 mg, 1.64 mmol), TBTU (540 mg, 1.68 mmol), TEA (1.00 mL, 7.2 mmol), THF (10 mL) and DMF (5 mL) are stirred for 5 min. Then trans-4-trifluoromethyl-cyclohexylamine (335 mg, 1.65 mmol) is added and it is stirred for 30 min. Water is added, the mixture is concentrated and the precipitate is filtered, washed with water and dried at 55° C.

Workup

  1. stirringit is stirred for 30 min
  2. concentrationthe mixture is concentrated
  3. filtrationthe precipitate is filtered
  4. washwashed with water
  5. customdried at 55° C.

Sources & evidence

ORD record
ord-ef2e87da43b24340965ab2eb288af87d
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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