Diisopropylethylamine → HCID 19076493, compound

HRID 234550Notes

Reaction equation

HRID 234550 reaction equation
[NH2:1][C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH3:13])[CH:9]=2)[N:4]([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[C:3]1=[O:24].CCN(C(C)C)C(C)C.Cl.Cl.[NH2:43][C:44]([CH3:52])([CH3:51])[CH2:45][N:46]([CH2:49][CH3:50])[CH2:47][CH3:48].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.C(N(CC)CC)C>[NH2:1][C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH3:13])[CH:9]=2)[N:4]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19](=[O:21])[NH:43][C:44]([CH3:52])([CH3:51])[CH2:45][N:46]([CH2:49][CH3:50])[CH2:47][CH3:48])=[CH:22][CH:23]=2)[C:3]1=[O:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19076400HCID 19076400, compoundHCID 19076479HCID 19076479, compound

Product 1

HCID 19076493HCID 19076493, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 0.896 g of the compound obtained in step B of EXAMPLE 262 in 10 ml of DCM is cooled to 0° C. and 0.36 ml of DIPEA is added, followed by 0.445 g of 2-amino-1-(diethylamino)-2-methylpropane dihydrochloride and then by 1.14 ml of triethylamine and 0.906 g of BOP. The mixture is stirred for 1 hour at RT and concentrated under vacuum. The residue is taken up with AcOEt, the organic phase is washed with a 5% solution of potassium carbonate, with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using AcOEt and then an AcOEt/MeOH mixture (80/20; v/v) as the eluent to give 0.12 g of the expected product after crystallization from a DCM/hexane mixture. M.p.=59° C.

Workup

  1. concentrationconcentrated under vacuum
  2. washthe organic phase is washed with a 5% solution of potassium carbonate, with water and with a saturated solution of NaCl
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-eafa5089f31c434987e7f955ed51fecc
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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