1-Hydroxybenzotriazole → HCID 18621203, compound

HRID 1861996Notes

Reaction equation

HRID 1861996 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](C2N3C(C(O)=O)=CN=C3CC2)=[CH:5][C:4]=1F)#[N:2].[Cl:21][C:22]1[CH:35]=[CH:34][C:33]([O:36][Si:37]([C:50]([CH3:53])([CH3:52])[CH3:51])([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:32][C:23]=1[CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C:26]1=[O:31].[CH3:54][CH2:55][N:56]=[C:57]=[N:58][CH2:59][CH2:60][CH2:61]N(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.[C:85]([O-])(O)=[O:86].[Na+]>CN(C=O)C>[Cl:21][C:22]1[CH:35]=[CH:34][C:33]([O:36][Si:37]([C:50]([CH3:53])([CH3:52])[CH3:51])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:32][C:23]=1[CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:85]([CH:59]2[N:58]3[C:54]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)=[CH:55][N:56]=[C:57]3[CH2:61][CH2:60]2)=[O:86])[CH2:27][C:26]1=[O:31]

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18621184HCID 18621184, compoundHCID 23001304HCID 23001304, compound

Product 1

HCID 18621203HCID 18621203, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carboxylic acid from Step M (1.02 g, 3.76 mmol), amine from Step F (1.80 g, 3.76 mmol), EDC hydrochloride (865 mg, 4.51 mmol), HOBT (610 mg, 4.51 mmol), and N,N-diisopropylethylamine (3.28 mL, 18.8 mmol) were stirred in dry DMF (20 mL) at 25° C. for 72 hours. The reaction was poured onto aq. NaHCO3 (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by column chromatography (1→5% MeOH/CH2Cl2) to provide the title compound as a yellow oil.

Workup

  1. extractionextracted with methylene chloride (3×50 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (1→5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-330a009c2bc14b65a3902be42c48aa8c
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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