Diethyl Ether → HCID 66978090, compound

HRID 576888Notes

Reaction equation

HRID 576888 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH:21]2[N:15]([N:16]([CH3:49])[C@@H:17]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41]CC4C=CC=CC=4)=[CH:37][CH:36]=3)[C:18](=[O:33])[N:19]([CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH2:20]2)[C:14](=[O:50])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.CCCCCC>C(O)(=O)C.Br>[CH2:1]([NH:8][C:9]([N:11]1[CH:21]2[N:15]([N:16]([CH3:49])[C@@H:17]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=3)[C:18](=[O:33])[N:19]([CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH2:20]2)[C:14](=[O:50])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8058HexaneHCID 66978357HCID 66978357, compound2×

Product 1

HCID 66978090HCID 66978090, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

(2S)—N-benzyl-2-(4-(benzyloxy)benzyl)-1-methyl-4-(naphthalen-1-ylmethyl)-3,9-dioxooctahydropyrimido[1,2-b][1,2,5]triazepine-6(7H)-carboxamide (Compound 1-267) 33 mg (0.05 mmol) was dissolved in 25% HBr acetic acid solution 0.2 ml and the mixture was stirred at room temperature for 5 hr. Ether 1.2 ml and n-hexane 0.8 ml were added to the reaction mixture and the mixture was concentrated in vacuo. The precipitation was purified on silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain the title compound 7.3 mg (yield 25%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe precipitation
  3. customwas purified on silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-76418788d5ba4152a9229bad856894ca
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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