Hydrochloric Acid → HCID 58299570, compound

HRID 79177Notes

Reaction equation

HRID 79177 reaction equation
[C:1]([C:3]1[C:8]2[N:9]([CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]3[N:11]=[C:12]([NH:16][C:17]4[N:22]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:13]=[CH:14][C:15]=3[C:7]=2[CH:6]=[CH:5][N:4]=1)#[N:2].Cl>CO>[CH:36]1([N:9]2[C:10]3[N:11]=[C:12]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([N:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)=[CH:21][N:22]=4)[N:13]=[CH:14][C:15]=3[C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:1]#[N:2])[C:8]2=3)[CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58299582HCID 58299582, compound

Product 1

HCID 58299570HCID 58299570, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 288 (44.0 mg, 81.5 μmol) was suspended in 3 mL methanol. Mmethanol saturated at room temperature with HCl (1 mL) was added, and the reaction stirred at room temperature for 2.5 hours. The solvents were removed in vacuo. The residue was taken up in methanol (10 mL) and stripped again to give compound 286 as a yellow solid (37 mg, 91%). 1H NMR (500 MHz, DMSO-d6) δ 1.68-1.80 (m, 2 H) 2.01-2.20 (m, 4 H) 2.64 (none, 2 H) 3.25-3.34 (m, 4 H) 3.34-3.44 (m, 5 H) 5.62-5.73 (m, 1 H) 7.60-7.73 (m, 1 H) 7.98-8.07 (m, 1 H) 8.09-8.16 (m, 1 H) 8.39-8.48 (m, 1 H) 8.58-8.65 (m, 1 H) 8.67-8.80 (m, 2 H) 9.40-9.49 (m, 1 H) 10.32-10.51 (m, 1 H) ppm.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-674122e82468406fadf59ce85b1e8160
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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