Ammonium Chloride → 2'-chloro-9'-cyclopentyl-8',9'-dihydrospiro[cyclobutane-1,7'-pyrimido[4,5-b][1, 4]diazepin]-6'(5'H)-one

HRID 1044092Notes

Reaction equation

HRID 1044092 reaction equation
C[O:2][C:3]([C:5]1([CH2:9][N:10]([C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][N:19]=[C:18]([Cl:25])[N:17]=2)[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:7][CH2:6]1)=O.[NH4+].[Cl-]>C(O)C.[Fe]>[Cl:25][C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:3](=[O:2])[C:5]3([CH2:8][CH2:7][CH2:6]3)[CH2:9][N:10]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:16]=2[N:17]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 581538851-{[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclobutanecarboxylic acid methyl ester

Product 1

HCID 579700082'-chloro-9'-cyclopentyl-8',9'-dihydrospiro[cyclobutane-1,7'-pyrimido[4,5-b][1, 4]diazepin]-6'(5'H)-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Reaction of 1-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-cyclobutanecarboxylic acid methyl ester with NH4Cl and iron powder in ethanol gave 2′-chloro-9′-cyclopentyl-8′,9′-dihydrospiro[cyclobutane-1,7′-pyrimido[4,5-b][1,4]diazepin]-6′(5′H)-one, isolated directly.

Sources & evidence

ORD record
ord-60a48ba26416438ba5d08a206c6775a4
Source dataset
uspto-grants-2013_10
Patent number
US08563542B2

Reaction notes

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