Acetohydrazide → HCID 66653586, compound

HRID 409542Notes

Reaction equation

[C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(CC)C(C)C)(C)C.[O:37]=[C:38]1[N:47]([CH2:48][CH2:49][CH3:50])[C:46](=[O:51])[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:52]([C:54]3[N:58]4[CH:59]=[CH:60][CH:61]=[CH:62][C:57]4=[C:56]([C:63]4[CH:64]=[C:65]([CH:69]=[CH:70][CH:71]=4)[C:66](O)=[O:67])[N:55]=3)=[O:53])[CH:44]=2)[NH:39]1>CN(C=O)C>[C:1]([NH:4][NH:5][C:66](=[O:67])[C:65]1[CH:69]=[CH:70][CH:71]=[C:63]([C:56]2[N:55]=[C:54]([C:52]([C:43]3[CH:44]=[C:45]4[C:40](=[CH:41][CH:42]=3)[NH:39][C:38](=[O:37])[N:47]([CH2:48][CH2:49][CH3:50])[C:46]4=[O:51])=[O:53])[N:58]3[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=23)[CH:64]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

29.6 mg (0.4 mmol) of acetohydrazide, 98.4 mg (0.3 mmol) of TOTU and 0.104 ml (0.6 mmol) of N,N-diisopropylethylamine are added, under an inert atmosphere, at 0° C., to 93.7 mg (0.2 mmol) of 3-{3-[(2,4-dioxo-3-propyl-1,2,3,4-tetrahydroquinazolin-6-yl)carbonyl]imidazo[1,5-a]pyridin-1-yl}benzoic acid in 6 ml of DMF. The reaction medium is stirred for 1 hour at 0° C. and then for 6 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in 10 ml of methanol. The precipitate obtained is filtered off, washed with dyethyl ether and with pentane, and then dried under reduced pressure at 40° C. overnight. 45 mg of a yellow solid are obtained.

Workup

waitfor 6 hours at 50° C.
concentrationconcentrated under reduced pressure
customThe precipitate obtained
filtrationis filtered off
washwashed with dyethyl ether and with pentane
customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record: ord-86564e83b7f44601926a897d6e7750f3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759344B2

Reaction notes

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