Diisopropylethylamine → HCID 59486429, compound

HRID 1694314Notes

Reaction equation

HRID 1694314 reaction equation
CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[CH:40]=[C:39]([S:44]([N:47]1[CH2:52][CH2:51][N:50]3[CH:53]=[CH:54][CH:55]=[C:49]3[CH:48]1[CH2:56][C:57](O)=[O:58])(=[O:46])=[O:45])[CH:38]=[CH:37]2.[N:60]1([CH2:66][C:67]2[CH:68]=[C:69]3[C:74](=[CH:75][CH:76]=2)[C@H:73]([NH2:77])[CH2:72][CH2:71][CH2:70]3)[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>C(Cl)Cl>[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[CH:40]=[C:39]([S:44]([N:47]1[CH2:52][CH2:51][N:50]3[CH:53]=[CH:54][CH:55]=[C:49]3[CH:48]1[CH2:56][C:57]([NH:77][C@H:73]1[C:74]3[C:69](=[CH:68][C:67]([CH2:66][N:60]4[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]4)=[CH:76][CH:75]=3)[CH2:70][CH2:71][CH2:72]1)=[O:58])(=[O:45])=[O:46])[CH:38]=[CH:37]2

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56594240(1R)-6-[(Piperidin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-1-amineHCID 594864212-(2-(6-Methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid

Product 1

HCID 59486429HCID 59486429, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

DIPEA (2.5 eq.), HOAt (1.0 eq.) and EDCl (1.5 eq.) were added to a solution of 2-(2-(6-methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)-acetic acid S2 (0.195 mmol, 1.0 eq.) in DCM (3 ml) at 0° C. and the mixture was stirred for 15 min at RT. Then (R)-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydro-naphthalen-1-amine A6 (0.234 mmol, 1.2 eq.) in DCM (2 ml) was added at 0° C. and the mixture was stirred overnight at RT. The reaction mixture was diluted with DCM and extracted with aqueous NaHCO3 solution, aqueous NH4Cl solution, water and saturated NaCl solution. The organic phase was dried (Na2SO4), concentrated to small volume and purified by column chromatography (alox). Yield: 55%; m/z=627.4 [MH]+

Workup

  1. extractionextracted with aqueous NaHCO3 solution, aqueous NH4Cl solution, water and saturated NaCl solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated to small volume
  4. custompurified by column chromatography (alox)

Sources & evidence

ORD record
ord-4ddd0ebc53af424aae12e33090d26fac
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

Loading…