Dichloromethane → HCID 135710756, compound

HRID 129500Notes

Reaction equation

[CH3:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[C:16]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH2:27][C:28]#[CH:29])=[O:24])[CH2:19][C:17]=3[S:18][C:5]=2[NH:4][C:3]1=O.C(=O)([O-])O.[Na+].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:37].ClCCl>C(COC)OC.CO>[CH3:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[C:16]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH2:27][C:28]#[CH:29])=[O:24])[CH2:19][C:17]=3[S:18][C:5]=2[NH:4][C:3]1=[S:37]

Participants

Conditions

Temperature: 80 °C

Procedure

0.21 g of 3-methyl-5-(2-chlorophenyl)-8-(3-butynyloxycarbonyl)-6,7,8,9-tetrahydro-1H,3H-pyrido[4',3':4,5]thieno[3,2-f][1,4]diazepin-2-one was dissolved in 10 ml of dimethoxyethane, to which 0.11 g of sodium hydrogencarbonate and 0.22 g of phosphorus pentasulfide were added, followed by heating at 80° C. for 3 hours. After completion of the reaction, dichloromethane and methanol were added, and the mixture was filtered, followed by addition of silica gel to the resultant filtrate and evaporating the solvent to dryness. Silica gel column chromatography (elution solvent: dichloromethane:methanol=99:1) was used for purification, thereby obtaining 0.15 g of the intended compound.

Workup

additionwere added
additionwere added
filtrationthe mixture was filtered
additionfollowed by addition of silica gel to the resultant filtrate
customevaporating the solvent to dryness
washSilica gel column chromatography (elution solvent: dichloromethane:methanol=99:1)
customwas used for purification

Sources & evidence

ORD record: ord-5fcd0af0c55d40db9cb4d0360efa2a23
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468740

Reaction notes

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