Triethylamine → HCID 141559958, compound

HRID 653556Notes

Reaction equation

HRID 653556 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)\[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:12](CI)[CH2:13][S:14](=[O:15])[C@H:9]12)=[O:6].Br.[OH:62][C:63]1[CH:64]=[C:65]2[C:69](=[CH:70][CH:71]=1)[CH2:68][NH:67][CH2:66]2.C(N(CC)CC)C>CN(C)C=O>[CH3:1][O:2]/[N:3]=[C:4](/[C:36]1[N:37]=[C:38]([NH:41][C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[S:39][CH:40]=1)\[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[C:12]([N:67]3[CH2:66][C:65]4[C:69](=[CH:70][CH:71]=[C:63]([OH:62])[CH:64]=4)[CH2:68]3)[CH2:13][S:14](=[O:15])[C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13982441HCID 13982441, compoundHCID 18630974105358-58-5

Product 1

HCID 141559958HCID 141559958, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.4 g (2.53 mmol) of the powder obtained in Example 1 (B) was dissolved in 20 ml of N,N-dimethylformamide, and 0.77 g (3.56 mmol) of 5-hydroxyisoindoline hydrobromide and 0.6 ml (4.3 mmol) of triethylamine were added thereto. The mixture was stirred at room temperature for 1 hour. The dimethylformamide was distilled off under reduced pressure. The residue was subjected to silica gel flush column chromatography (ethyl acetate/n-hexane =3/1 to 1/0) to obtain 2.1 g (yield: 87%) of the above-identified compound.

Workup

  1. distillationThe dimethylformamide was distilled off under reduced pressure
  2. customflush column chromatography (ethyl acetate/n-hexane =3/1 to 1/0)

Sources & evidence

ORD record
ord-69303ec640354e30a09ff8d4d32a0a64
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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