Cyclobutanol → HCID 70674457, compound

HRID 1747723Notes

Reaction equation

ClC([O:5][C:6](=O)[O:7]C(Cl)(Cl)Cl)(Cl)Cl.[CH:13]1([OH:17])[CH2:16][CH2:15][CH2:14]1.Cl.Cl.Cl.[F:21][C:22]1[CH:46]=[CH:45][CH:44]=[CH:43][C:23]=1[CH2:24][C:25]1[N:29]2[N:30]=[CH:31][CH:32]=[CH:33][C:28]2=[C:27]([C:34]2[N:39]=[C:38]([NH2:40])[C:37]([NH2:41])=[C:36]([NH2:42])[N:35]=2)[N:26]=1.[C:47](=O)(O)[O-:48].[Na+]>N1C=CC=CC=1>[CH:6]([OH:7])=[O:5].[NH2:42][C:36]1[C:37]([NH:41][C:47](=[O:48])[O:17][CH:13]2[CH2:16][CH2:15][CH2:14]2)=[C:38]([NH2:40])[N:39]=[C:34]([C:27]2[N:26]=[C:25]([CH2:24][C:23]3[CH:43]=[CH:44][CH:45]=[CH:46][C:22]=3[F:21])[N:29]3[C:28]=2[CH:33]=[CH:32][CH:31]=[N:30]3)[N:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

42 mg (0.14 mmol) of bis(trichloromethyl)carbonate were added to 27.3 mg (0.38 mmol) of cyclobutanol, and the mixture was cooled to 0° C. At this temperature, 31 μl (0.38 mmol) of pyridine were added slowly, and the mixture was then stirred at 20° C. for one hour. The mixture was then cooled again to 0° C., and a solution of 100 mg (0.25 mmol) of 2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]pyrimidine-4,5,6-triamine (Example 9A) in 1 ml of pyridine was added. The reaction mixture was stirred in an ice bath for 10 minutes, and 2 ml of saturated aqueous sodium bicarbonate solution were then added. The concentrated reaction was purified by preparative HPLC (acetonitrile:water (+0.1% formic acid) gradient). This gave 25 mg (20% of theory) of the target compound.

Workup

temperatureThe mixture was then cooled again to 0° C.
stirringThe reaction mixture was stirred in an ice bath for 10 minutes
customThe concentrated reaction
customwas purified by preparative HPLC (acetonitrile:water (+0.1% formic acid) gradient)

Sources & evidence

ORD record: ord-c713feeea0d84a24bf9f3cd536ada051
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150580B2

Reaction notes

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