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Diisopropylethylamine → HCID 58577219, compound

HRID 511194
Notes
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Reaction equation

HRID 511194 reaction equation
[Li+].[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=C[C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([O-:21])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.F[P-](F)(F)(F)(F)F.C[N:32](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:21])[CH2:18][CH2:17][CH2:16][N:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:22])[F:23])=[CH:9][N:32]=4)[CH2:15][CH2:14]3)[CH2:50][CH2:51]2)[CH:63]=[CH:62][C:59]=1[C:60]#[N:61]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 585760704-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid lithium saltHCID 66671763HCID 66671763, compound

Product 1

HCID 58577219
HCID 58577219, compound
Yield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-butyric acid lithium salt (17 mg; 0.05 mmol, prepared in accordance with Example 3) in tetrahydrofuran (1.0 mL) is added 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 (0.5 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 stiffing 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 (9 mg; 0.016 mmol). The structure was confirmed using Protocol I-D. Calculated mass=569; observed mass=569; HPLC retention time=1.48 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-4263852b88cb46c78a85689ccb914140
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096524B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes