Diisopropylethylamine → HCID 178457048, compound

HRID 1641318Notes

Reaction equation

HRID 1641318 reaction equation
[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[C:10](=[O:25])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH:35]([C:37]1[CH:38]=[C:39]([CH2:43][CH:44]([CH3:47])[C:45]#[N:46])[CH:40]=[CH:41][CH:42]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([NH:7][C:8]2[C:12]3([CH2:13][CH2:14][N:15]([CH2:35][C:37]4[CH:38]=[C:39]([CH2:43][CH:44]([CH3:47])[C:45]#[N:46])[CH:40]=[CH:41][CH:42]=4)[CH2:16][CH2:17]3)[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[C:10](=[O:25])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58949905HCID 58949905, compoundHCID 178517964HCID 178517964, compound

Product 1

HCID 178457048HCID 178457048, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a 20 mL dichloroethane solution of 0.35 g (0.92 mmol) 4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one and 0.25 mL (1.4 mmol) DIEA went 0.16 g (0.92 mmol) 3-(3-formylphenyl)-2-methylpropanenitrile (9-3). The suspension was allowed to stir for 10 min then 0.4 g (1.9 mmol) sodium triacetoxyborohydride was added and the reaction was allowed to stir at rt overnight. HPLC/MS showed no starting material so the reaction was quenched with 100 mL sat NaHCO3 and diluted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The remaining oil was purified on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluted with 5% MeOH+0.5M NH3 in CH2Cl2 at 25 mL/min over 30 min. The product eluted second.

Workup

  1. stirringto stir at rt overnight
  2. customwas quenched with 100 mL
  3. additiondiluted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe remaining oil was purified on an Isco automated system
  9. washeluted with 5% MeOH+0.5M NH3 in CH2Cl2 at 25 mL/min over 30 min
  10. washThe product eluted second

Sources & evidence

ORD record
ord-08c10c1b14bf4c27ba94073a3c3b9f98
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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