Triethylamine → HCID 87279507, compound

HRID 2040342Notes

Reaction equation

HRID 2040342 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:46]=[C:45]([N:47]4[CH2:52][CH2:51][N:50]([CH2:53][C:54]5[CH2:59][CH2:58][C:57]([CH3:61])([CH3:60])[CH2:56][C:55]=5[C:62]5[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=5)[CH2:49][CH2:48]4)[CH:44]=[CH:43][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]4[CH2:39][CH2:38][C:30]5([CH2:35][O:34]C(C)(C)[O:32][CH2:31]5)[CH2:29][CH2:28]4)=[C:21]([N+:40]([O-:42])=[O:41])[CH:20]=3)(=[O:18])=[O:17])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>ClCCl>[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:46]=[C:45]([N:47]4[CH2:48][CH2:49][N:50]([CH2:53][C:54]5[CH2:59][CH2:58][C:57]([CH3:60])([CH3:61])[CH2:56][C:55]=5[C:62]5[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=5)[CH2:51][CH2:52]4)[CH:44]=[CH:43][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]4[CH2:39][CH2:38][C:30]([CH2:31][OH:32])([CH2:35][OH:34])[CH2:29][CH2:28]4)=[C:21]([N+:40]([O-:42])=[O:41])[CH:20]=3)(=[O:18])=[O:17])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 87279736HCID 87279736, compound

Product 1

HCID 87279507HCID 87279507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 391G (680 mg) in dichloromethane (3514 μl) was added para-toluenesulfonic acid monohydrate (535 mg) and the reaction was allowed to stir for 3 hours. Triethylamine (490 μl) was added and the reaction was concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix 0.5-5% dichloromethane/methanol). 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 11.69 (s, 1H) 8.35 (s, 1H) 8.03 (d, 2H) 7.46-7.58 (m, 3H) 7.29-7.42 (m, 3H) 7.04 (d, 2H) 6.68 (dd, 1H) 6.39 (d, 1H) 6.20 (s, 1H) 4.19-4.35 (m, 2H) 4.05 (d, 2H) 3.37 (d, 2H) 3.17 (d, 2H) 3.09 (bs, 4H) 2.10-2.31 (m, 6H) 1.96 (bs, 2H) 1.62-1.75 (m, 1H) 1.46-1.62 (m, 4H) 1.39 (t, 2H) 1.05-1.32 (m, 4H) 0.93 (s, 6H).

Workup

  1. concentrationthe reaction was concentrated by rotary evaporation
  2. customThe residue was purified by regular phase flash column chromatography (Analogix 0.5-5% dichloromethane/methanol)

Sources & evidence

ORD record
ord-44dd5f55fd8943a6bc9983e493f9103e
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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