Diisopropylethylamine → HCID 46909276, compound

HRID 1694313Notes

Reaction equation

HRID 1694313 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)[CH2:73][CH:72]([NH2:77])[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][CH:72]1[CH2:71][CH2:70][C:69]3[C:74](=[CH:75][CH:76]=[C:67]([CH2:66][N:60]4[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]4)[CH:68]=3)[CH2:73]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 59486397HCID 59486397, compoundHCID 594864212-(2-(6-Methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid

Product 1

HCID 46909276HCID 46909276, compoundYield 58%

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 (0.2325 mmol, 1.0 eq.) in DCM (3 ml) at 0° C. and the mixture was stirred for 15 min at RT. Then 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-amine A5 (0.2325 mmol, 1.0 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 sodium chloride solution. The organic phase was dried (Na2SO4), concentrated to small volume and purified by column chromatography (alox). Yield: 58%; m/z=627.4 [MH]+

Workup

  1. extractionextracted with aqueous NaHCO3 solution, aqueous NH4Cl solution, water and saturated sodium chloride 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-24401637caa449fa97e078cbec5ae423
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

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