Diisopropylethylamine → HCID 178521459, compound

HRID 1047377Notes

Reaction equation

HRID 1047377 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][C:21](O)=[O:22])[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)([F:4])[F:3].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:48][C:49]([F:63])([F:62])[C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)=[CH:52][CH:51]=1.C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.C(OCC)C>[F:63][C:49]([F:48])([F:62])[C:50]1[CH:51]=[CH:52][C:53]([N:56]2[CH2:61][CH2:60][N:59]([C:21](=[O:22])[CH2:20][O:19][C@H:16]3[CH2:15][CH2:14][C@H:13]([NH:12][C:9]4[CH:10]=[CH:11][C:6]([S:5][C:2]([F:1])([F:3])[F:4])=[CH:7][CH:8]=4)[CH2:18][CH2:17]3)[CH2:58][CH2:57]2)=[CH:54][CH:55]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1217181-(4-(Trifluoromethyl)phenyl)piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 178526001HCID 178526001, compound

Product 1

HCID 178521459HCID 178521459, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[Trans-4-(4-trifluoromethylsulfanyl-phenylamino)-cyclohexyloxy]-acetic acid (18 mg, 0.05 mmol, prepared in accordance with Example 30) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (19 mg, 0.05 mmol) were dissolved in dry tetrahydrofuran (2 mL) and stirred at room temperature for 10 min. 1-(4-Trifluormethyl-phenyl)-piperazine (12 mg, 0.05 mmol) and diisopropylethylamine (18 μL, 0.10 mmol) were then added, and the solution was stirred at room temperature for 1.5 hr. Aluminium oxide was then added (1 spatula). Afterward, the mixture was diluted with diethylether (10 mL) and filtered. The filtrate was concentrated under vacuum. The crude product was purified by preparative HPLC. Following lyophilization of the fractions of interest, the desired product was isolated as a solid (16 mg, 57% yield). The structure was confirmed using Protocol I-B. Calculated mass=562; observed mass=562; HPLC retention time=6.03 min.

Workup

  1. stirringthe solution was stirred at room temperature for 1.5 hr
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-465654bd9db9454aa4cf4189a724ad92
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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