Diisopropylethylamine → HCID 140609640, compound

HRID 1050931Notes

Reaction equation

HRID 1050931 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][OH:15])[CH2:6]N.[C:16]([O:20][C:21]([NH:23][C:24](C1C=CNN=1)=[N:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:22])([CH3:19])([CH3:18])[CH3:17].CC[N:40](C(C)C)C(C)C>CO>[C:29]([O:28][C:26]([N:25]([CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][CH2:14][OH:15])=[C:3]([Br:2])[CH:4]=1)[C:24]([NH:23][C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22])=[NH:40])=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 89613725HCID 89613725, compoundHCID 178454276N,N'-bis-BOC-pyrazole carboxamidine

Product 1

HCID 140609640HCID 140609640, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 2 (0.438 g, 1.48 mmol) was dissolved in MeOH (7.00 mL), and successively treated with N,N′-bis-tert-butoxycarbonyl-1H-pyrazole carboxamidine (0.412 g, 1.33 mmol) and i-Pr2NEt (0.380 g, 2.95 mmol) at ambient temperature. The resulting mixture was stirred 3 h then concentrated and purified by chromatography on SiO2 (A: hexanes; B: EtOAc; 0-100% B over 19.2 min; 40 mL/min; 40 g column) to obtain the product as a white foam (0.61 g, 82%). 1H NMR (300 MHz, CDCl3) δ 8.5 (t, 1H), 7.5 (d, 1H), 7.2 (dd, 1H), 6.85 (d, 1H), 4.52 (d, 2H), 4.18 (t, 2H), 3.9 (t, 2H), 2.1 (m, 2H), 1.52 (s, 9H), 1.47 s (s, 9H).

Workup

  1. concentrationthen concentrated
  2. custompurified by chromatography on SiO2 (A: hexanes
  3. wait0-100% B over 19.2 min

Sources & evidence

ORD record
ord-ed2d2725f114430092e1669f2817e8d1
Source dataset
uspto-grants-2016_07
Patent number
US09388125B2

Reaction notes

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