Tert-butyl 1,4-diazepane-1-carboxylate → 4-[[3-[(Hexahydro-1H-1,4-diazepin-1-yl)carbonyl]phenyl]methyl]-1(2H)-phthalazinone

HRID 1012973Notes

Reaction equation

HRID 1012973 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)C(O)=O)=[N:4][NH:3]1.[N:22]1([C:29](OC(C)(C)C)=[O:30])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[N:22]1([C:29]([C:15]2[CH:14]=[C:13]([CH:21]=[CH:20][CH:19]=2)[CH2:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[NH:3][N:4]=2)=[O:30])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 251319063-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid

Product 1

HCID 251322564-[[3-[(Hexahydro-1H-1,4-diazepin-1-yl)carbonyl]phenyl]methyl]-1(2H)-phthalazinoneYield 97%

Procedure

The synthesis was carried out according to the method described in (a) above using 3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)benzoic acid (A) and tert-butyl 1-homopiperazine carboxylate to yield 4-[3-([1,4]diazepane-1-carbonyl)benzyl]-2H-phthalazin-1-one (3) as a grey crystalline solid (5.3 g, 97%); m/z [M+1]+ 363 (97% purity); δH 2.6-3.8 (10H, m), 4.4 (2H, s), 7.2-7.5 (4H, m), 7.7-8.0 (3H, m), 8.2-8.3 (1H, m), 12.6 (1H, s)

Sources & evidence

ORD record
ord-52d47f10a2c84959aa80f054b25dd4e9
Source dataset
uspto-grants-2011_07
Patent number
US07981889B2

Reaction notes

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