Triethylamine → HCID 59722550, compound

HRID 1664943Notes

Reaction equation

C(N(CC)CC)C.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([CH2:26][C:27]([F:30])([F:29])[F:28])=[N:24][N:25]=[C:20]2[C@H:19]([NH2:31])[CH2:18][CH2:17]1.[C:32]([N:39]1[CH:43]=[CH:42]N=[CH:40]1)(N1C=CN=C1)=[O:33].[CH3:44][C:45]1[CH:46]=[C:47]([CH:52]2CCNC[CH2:53]2)[C:48](=[O:51])[NH:49][N:50]=1>O1CCCC1.ClCCl>[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([CH2:26][C:27]([F:30])([F:28])[F:29])=[N:24][N:25]=[C:20]2[C@H:19]([NH:31][C:32]([N:39]2[CH2:40][CH2:53][CH:52]([C:47]3[C:48](=[O:51])[NH:49][N:50]=[C:45]([CH3:44])[CH:46]=3)[CH2:42][CH2:43]2)=[O:33])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 60 °C

Procedure

Triethylamine (42 μL, 0.298 mmol) was added to a solution of the bis hydrochloride salt of (6S,9R)-6-(2,3-difluorophenyl)-3-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-amine (50 mg, 0.119 mmol) and 1,1′-carbonyldiimidazole (34 mg, 0.209 mmol) in tetrahydrofuran (2 mL) at 0° C. After 15 min, additional 1,1′-carbonyldiimidazole (10 mg, 0.062 mmol). After 30 min, 6-methyl-4-piperidin-4-ylpyridazin-3(2H)-one (28 mg, 0.143 mmol) and dichloromethane (3 mL) were added and the mixture heated to 60° C. After 1 h, the reaction mixture was allowed to cool to ambient temperature and concentrated. Purification by reverse phase HPLC (C-18, 10% acetonitrile/water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (54 mg). MS 566.2313 (M+1).

Workup

waitAfter 30 min
waitAfter 1 h
temperatureto cool to ambient temperature
concentrationconcentrated
customPurification by reverse phase HPLC (C-18, 10% acetonitrile/water→100% acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-07addd5f84d647df9a016f2b00b50a4a
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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