Diisopropylethylamine → HCID 18320690, compound

HRID 1699526Notes

Reaction equation

HRID 1699526 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](C(N=[N+]=[N-])=O)=[CH:5]1)[CH2:2][CH3:3].[C:18]([OH:21])(=O)C.[NH2:22][CH:23]([C:27]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH2:38][CH2:39][CH2:40][CH2:41][N:42]2[C:50](=[O:51])[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]2=[O:52])[CH:30]=1)=[O:28])[C:24]([NH2:26])=[O:25].C([N:55](C(C)C)C(C)C)C>C1C=CC=CC=1.C1COCC1>[O:51]=[C:50]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43](=[O:52])[N:42]1[CH2:41][CH2:40][CH2:39][CH2:38][N:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([C:27](=[O:28])[CH:23]([NH:22][C:18]([NH:55][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH2:1][CH2:2][CH3:3])[CH:5]=2)=[O:21])[C:24]([NH2:26])=[O:25])=[CH:30]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 17902684HCID 17902684, compoundHCID 18320673HCID 18320673, compound

Product 1

HCID 18320690HCID 18320690, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 57 mg (0.25 mmol) of the product of step c) in 5 ml of benzene was heated to 95° C. for 5 hours. After cooling to room temperature the benzene solution was rapidly added to a freshly prepared suspension of 120 mg (0.24 mmol) of the product of step b) and 31 mg (0.24 mmol) of ethyldiisopropylamine in 10 ml of THF. The resulting solution was stirred for 2 hours. The solvents were evaporated and the residue suspended in 20 ml of water and stirred for 10 minutes. The product was filtered and dried, giving 130 mg (84%) of the sub-title compound as a yellowish solid.

Workup

  1. customThe solvents were evaporated
  2. stirringstirred for 10 minutes
  3. filtrationThe product was filtered
  4. customdried

Sources & evidence

ORD record
ord-f7dbe04290fe49fd8911667885c6eb32
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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