Triethylamine → HCID 12094440, compound

HRID 736924Notes

Reaction equation

HRID 736924 reaction equation
[NH2:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:5]([CH2:6][C@@H:7]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]([O-])=[O:9])=[CH:4][C:3]=1[Cl:25].C1[CH:27]=[CH:28][C:29]2[N:34](O)N=N[C:30]=2[CH:31]=1.C[N:37](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:58]([N:60]([CH2:63]C)[CH2:61][CH3:62])[CH3:59]>C1COCC1>[NH2:1][C:2]1[C:20]([C:21]([F:23])([F:22])[F:24])=[CH:19][C:5]([CH2:6][C@H:7]([C:8]([N:37]2[CH2:27][CH2:28][CH:29]([N:34]3[CH2:62][CH2:61][N:60]([CH3:63])[CH2:58][CH2:59]3)[CH2:30][CH2:31]2)=[O:9])[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:4][C:3]=1[Cl:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86604292HCID 86604292, compound

Product 1

HCID 12094440HCID 12094440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.4 g (40.3 mmol) of 4-tert. butyl (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-succinate, 7.4 g (40.3 mmol) of (1-methyl-4-piperidin-4-yl)-piperazine, 5.45 g (40.3 mmol) of HOBt, 12.94 g (40.3 mmol) of TBTU, 11.77 mL (85.0 mmol) of triethylamine and 400 mL of THF was stirred for 12 h at RT. Then the mixture was evaporated down i. vac. and the residue remaining was distributed between EtOAc and NaHCO3 solution. The org. phase was separated off, dried and evaporated down i. vac. The residue obtained was purified by chromatography on aluminium oxide. The desired product was obtained in the form of a yellow oil.

Workup

  1. customThen the mixture was evaporated down i
  2. customphase was separated off
  3. customdried
  4. customevaporated down i
  5. customThe residue obtained
  6. customwas purified by chromatography on aluminium oxide

Sources & evidence

ORD record
ord-318cd301dc6c45568eb1c5514b4f8a7c
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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