Diisopropylethylamine → HCID 58577101, compound

HRID 511193Notes

Reaction equation

HRID 511193 reaction equation
[Li+].[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][C:19]([O-])=[O:20])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.F[P-](F)(F)(F)(F)F.CN(C)C(ON1C2C=CC=CC=2N=N1)=[N+](C)C.Cl.[NH:49]1[CH2:54][CH2:53][CH:52]([NH:55][C:56]2[CH:63]=[CH:62][C:59]([C:60]#[N:61])=[C:58]([C:64]([F:67])([F:66])[F:65])[CH:57]=2)[CH2:51][CH2:50]1.C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[F:67][C:64]([F:65])([F:66])[C:58]1[CH:57]=[C:56]([NH:55][CH:52]2[CH2:53][CH2:54][N:49]([C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([F:23])([F:2])[F:22])=[CH:9][CH:8]=4)[CH2:15][CH2:14]3)[CH2:50][CH2:51]2)[CH:63]=[CH:62][C:59]=1[C:60]#[N:61]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 58576063HCID 58576063, compoundHCID 66671763HCID 66671763, compound

Product 1

HCID 58577101HCID 58577101, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-butyric acid lithium salt (16 mg; 0.05 mmol, prepared in accordance with Example 133) in tetrahydrofuran (1.0 mL) is added a solution of tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformamide (0.5 mL). 15 minutes later, a solution of 4-(piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile hydrochloride (15 mg; 0.05 mmol, prepared in accordance with Example 155) in dimethylformamide (10.5 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) is added. After 2 hours at room temperature, aluminium oxide (90 active basic) is added and stirring is continued. The solids are removed by filtration and the filtrate is concentrated under high vacuum. The obtained residue is purified by preparative HPLC to afford the desired compound (20 mg; 0.035 mmol). The structure was confirmed using Protocol I-D. Calculated mass=567; observed mass=567; HPLC retention time=2.17 min.

Workup

  1. customThe solids are removed by filtration
  2. concentrationthe filtrate is concentrated under high vacuum
  3. customThe obtained residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-7f1ce4f640144e5e891d8bdca1370d31
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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