Hexane → HCID 57786638, compound

HRID 1012950Notes

Reaction equation

HRID 1012950 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1.[N+:20]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])#[C-:21].CCCCCC.C(OCC)(=[O:37])C>C1COCC1>[CH2:26]([O:25][C:23](=[O:24])[CH:22]([NH:20][C:21]([NH:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:4]([CH2:5][C:6]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[NH:8][N:7]=2)[CH:3]=1)=[O:37])[CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl Acetate2×HCID 4571250Ethyl 2-isocyanopropanoateHCID 597557554-(3-Aminobenzyl)-5,6,7,8-tetrahydrophthalazin-1(2h)-one

Product 1

HCID 57786638HCID 57786638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(3-amino-benzyl)-5,6,7,8-tetrahydro-2H-phthalazin-1-one (4) (0.472 mg, 1.850 mmol) in dry THF (25 ml) was added a solution of ethyl 2-isocyanopropionate (266 mg, 1.850 mmol) in 2 ml of THF. The resultant solution was then stirred for 4 hours and then concentrated in vacuo to afford a brown oil. The crude oil was subjected to flash chromatography eluent 4:1, hexane:ethyl acetate. (Rf=0.14 neat ethyl acetate). Main peak in LC-MS, (7.20 g, 98% purity); m/z (LC-MS, ESP), RT=3.20 mins (M+H 389.4).

Workup

  1. concentrationconcentrated in vacuo
  2. customto afford a brown oil

Sources & evidence

ORD record
ord-15a296904f5f4e6597a883058231a751
Source dataset
uspto-grants-2011_07
Patent number
US07981890B2

Reaction notes

Loading…