1-Hydroxybenzotriazole → HCID 178451519, compound

HRID 243855Notes

Reaction equation

HRID 243855 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[N:17]=[C:18]([C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23](O)=[O:24])[NH:19][CH:20]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[NH3:8].[N:16]1[N:17]=[C:18]([C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23]([N:12]2[CH2:13][CH:14]3[CH2:15][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]3[CH2:11]2)=[O:24])[NH:19][CH:20]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 178524291HCID 178524291, compound

Product 2

HCID 222AmmoniaYield 8%HCID 178451519HCID 178451519, compoundYield 150%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 15 (1.0 g, 4.73 mmol) in DCM (24 mL) was added 2-(4H-[1,2,4]triazol-3-yl)benzoic acid (895 mg, 4.73 mmol) followed by EDCl (1.36 g, 7.09 mmol), HOBt (959 mg, 7.09 mmol) and TEA (1.97 mL, 14.19 mmol). The mixture was stirred for 14 h at room temperature and then washed 2× with saturated aqueous NH4Cl solution. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (DCM to 8% 2M NH3 in MeOH/DCM) afforded the desired product as a pale yellow foam (1.36 g, 75%). MS (ESI): mass calculated for C20H25N5O3, 383.45, m/z found 384.1 [M+1]+. 1H NMR (500 MHz, CDCl3): 12.62 (s, 1H), 8.19-8.03 (m, 2H), 7.56-7.44 (m, 2H), 7.39-7.32 (m, 1H), 3.96-2.72 (m, 10H), 1.53-1.35 (m, 9H).

Workup

  1. washwashed 2× with saturated aqueous NH4Cl solution
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-566c314c473144c895003b18946c3393
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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