Triethylamine → HCID 67997624, compound

HRID 718732Notes

Reaction equation

HRID 718732 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29](ON3C(=O)CCC3=O)=[O:30])C3C(=CC=CC=3)C=2C=CC=1.[ClH:40].[NH2:41][C:42]1[CH:50]=[CH:49][CH:48]=[C:47]2[C:43]=1[C:44](=[O:65])[N:45]([C:52]1([CH2:60][CH2:61][CH2:62][CH2:63][NH2:64])[CH2:57][CH2:56][C:55](=[O:58])[NH:54][C:53]1=[O:59])[C:46]2=[O:51].C(N(CC)CC)C>CS(C)=O>[NH2:41][C:42]1[CH:50]=[CH:49][CH:48]=[C:47]2[C:43]=1[C:44](=[O:65])[N:45]([C:52]1([CH2:60][CH2:61][CH2:62][CH2:63][NH:64][C:29](=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][NH2:17])[CH2:57][CH2:56][C:55](=[O:58])[NH:54][C:53]1=[O:59])[C:46]2=[O:51].[ClH:40].[NH2:41][C:42]1[CH:50]=[CH:49][CH:48]=[C:47]2[C:43]=1[C:44](=[O:65])[N:45]([C:52]1([CH2:60][CH2:61][CH2:62][CH2:63][NH2:64])[CH2:57][CH2:56][C:55](=[O:58])[NH:54][C:53]1=[O:59])[C:46]2=[O:51]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58572163HCID 58572163, compoundHCID 67997624HCID 67997624, compound

Product 2

HCID 67997499HCID 67997499, compoundYield 42%HCID 67997624HCID 67997624, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 23 (0.012 g, 0.022 mmol) in DMSO (2 mL) were added 7 (0.011 g, 0.0289 mmol) and triethylamine (0.01 mL, 0.071 mmol) under an atmosphere of argon, and the mixture was stirred at room temperature. After 16 h, the crude mixture was directly purified by preparative HPLC to afford 25 (0.005 g, 42%), 24 (0.0014 g, 8.2%) and unreacted 7 (0.0037 g, 48%). 1H NMR (400 MHz, DMSO) δ 8.39 (s, 2H), 7.86 (s, 1H), 7.49-7.37 (m, 1H), 7.04-6.82 (m, 2H), 6.53 (s, 2H), 3.59-3.36 (m, 11H), 3.03-2.93 (m, 2H), 2.84-2.76 (m, 2H), 2.33-2.16 (m, 5H), 2.05-1.96 (m, 2H), 1.44-1.31 (m, 3H), 1.25-1.16 (m, 3H). MS (ESI) m/z calcd for C26H38N5O8 [M+H]+ 548.6, found 548.5.

Workup

  1. customthe crude mixture was directly purified by preparative HPLC

Sources & evidence

ORD record
ord-fb4f42c3f4294b9f938765ed5c341de7
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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