1-Hydroxybenzotriazole → HCID 67116279, compound

HRID 244052Notes

Reaction equation

HRID 244052 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[C:8]([C:13]([OH:15])=O)=[N:9][CH:10]=[CH:11][CH:12]=2)[O:4][N:3]=1.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]2[CH2:31][CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[CH2:25]2)[N:18]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[NH3:3].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]2[CH2:31][CH:30]3[CH:26]([CH2:27][N:28]([C:13]([C:8]4[C:7]([C:5]5[O:4][N:3]=[C:2]([CH3:1])[N:6]=5)=[CH:12][CH:11]=[CH:10][N:9]=4)=[O:15])[CH2:29]3)[CH2:25]2)[N:18]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 662108752-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrroleHCID 67116519HCID 67116519, compound

Product 2

HCID 222AmmoniaYield 8%HCID 67116279HCID 67116279, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step C (60 mg, 0.30 mmol) in DCM (3 mL) was added Intermediate 23 (65 mg, 0.30 mmol) followed by EDCl (85 mg, 0.44 mmol), HOBt (60 mg, 0.44 mmol) and TEA (0.08 mL, 0.59 mmol). The mixture was stirred at room temperature for 14 h and then concentrated in vacuo. Chromatography (DCM to 8% 2 M NH3 in MeOH/DCM) afforded the desired compound as a colorless foam (49 mg, 41%). MS (ESI) mass calculated for C21H23N7O2, 405.19; m/z found, 406.2. 1H NMR (500 MHz, CDCl3): 8.82-8.75 (m, 1H), 8.42-8.36 (m, 1H), 7.52-7.47 (m, 1H), 6.31-6.26 (m, 1H), 4.02-3.90 (m, 2H), 3.86-3.79 (m, 1H), 3.76-3.69 (m, 2H), 3.66-3.54 (m, 2H), 3.24-3.18 (m, 1H), 3.14-2.99 (m, 2H), 2.48-2.42 (m, 3H), 2.33-2.24 (m, 6H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9669beccd81e47bbb205061cb3a845d8
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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