Diisopropylethylamine → HCID 89705260, compound

HRID 528691Notes

Reaction equation

HRID 528691 reaction equation
Cl.[CH3:2][C@:3]12[CH:16]3[CH2:17][CH:14]([C:15]3([CH3:19])[CH3:18])[CH2:13][C@H:4]1[O:5][B:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)[O:7]2.[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:30]([NH:32][CH2:33][C:34](O)=[O:35])=[O:31])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl>[O:35]=[C:34]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[B:6]1[O:5][C@@H:4]2[CH2:13][CH:14]3[CH2:17][CH:16]([C@:3]2([CH3:2])[O:7]1)[C:15]3([CH3:19])[CH3:18])[CH2:33][NH:32][C:30]([C:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]=[CH:21][CH:22]=1)=[O:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 75539583HCID 75539583, compoundHCID 81456049HCID 81456049, compound

Product 1

HCID 89705260HCID 89705260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-((3aS,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)pyrrolidine hydrochloride (0.190 g, 0.665 mmol) was added to a mixture of 2-(quinoline-4-carboxamido)acetic acid (0.153 g, 0.665 mmol), HATU (0.253 g, 0.665 mmol) and DIPEA (0.360 ml, 2.062 mmol) in dichloromethane (5 mL). The mixture was stirred for 3 h and washed with 0.5N citric acid, saturated sodium bicarbonate and brine, followed by filtration and evaporation. Purification was done using column chromatography DCM-MeOH 0-6% MeOH.

Workup

  1. washwashed with 0.5N citric acid, saturated sodium bicarbonate and brine
  2. filtrationfollowed by filtration and evaporation
  3. customPurification

Sources & evidence

ORD record
ord-f9b4a53875f44c9298d3e5c9e1426792
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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