1-Hydroxybenzotriazole → HCID 59483860, compound

HRID 1808389Notes

Reaction equation

HRID 1808389 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:32][C:33]1[S:37][C:36]([C:38](Cl)=[O:39])=[CH:35][CH:34]=1.[N:41]1[CH:46]=[CH:45][C:44]([N:47]2[CH2:75][CH2:74][C:50]3([CH2:55][CH2:54][N:53]([C:56]([C:58]4[N:59]=[C:60]5[CH2:65][N:64](C(OC(C)(C)C)=O)[CH2:63][CH2:62][N:61]5[CH:73]=4)=[O:57])[CH2:52][CH2:51]3)[CH2:49][CH2:48]2)=[CH:43][CH:42]=1>C(Cl)Cl>[Cl:32][C:33]1[S:37][C:36]([C:38]([N:64]2[CH2:63][CH2:62][N:61]3[CH:73]=[C:58]([C:56]([N:53]4[CH2:52][CH2:51][C:50]5([CH2:74][CH2:75][N:47]([C:44]6[CH:43]=[CH:42][N:41]=[CH:46][CH:45]=6)[CH2:48][CH2:49]5)[CH2:55][CH2:54]4)=[O:57])[N:59]=[C:60]3[CH2:65]2)=[O:39])=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59483777HCID 59483777, compound

Product 1

HCID 59483860HCID 59483860, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

EDCl (1.29 mmol, 1.5 equiv.), HOBt (1.29 mmol, 1.5 equiv.) and DIPEA (3.44 mmol, 4 equiv.) were added at 0° C. to a solution of 5-chlorothiophene-2-carbonyl chloride (0.86 mmol, 1.0 equiv.) in DCM (20 ml), and the mixture was stirred for 30 min. A solution of tert-butyl 2-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carbonyl)-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (0.86 mmol, 1.0 equiv.) in DCM (5 ml) was then added, the ice bath was removed, and stirring was carried out for 16 h at 25° C. The reaction mixture was diluted with dichloromethane (100 ml) and washed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (8% methanol in DCM) and the desired product was thus obtained in the form of a white solid. Yield: 11%. MS, Rt=2.7 min; m/z=525.2 [MH]+

Workup

  1. customthe ice bath was removed
  2. stirringstirring
  3. waitwas carried out for 16 h at 25° C
  4. additionThe reaction mixture was diluted with dichloromethane (100 ml)
  5. washwashed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (8% methanol in DCM)

Sources & evidence

ORD record
ord-70aa3c10100c4a61acdba52889d4b8b7
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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