Triethylamine → HCID 59722684, compound

HRID 1664939Notes

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](N1C=CN=C1)(N1C=CN=C1)=[O:33].[NH:44]1[CH2:49][CH2:48][CH:47]([N:50]2[CH2:56][CH2:55][C:54]3[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=3[NH:52][C:51]2=[O:61])[CH2:46][CH2:45]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:44]2[CH2:45][CH2:46][CH:47]([N:50]3[CH2:56][CH2:55][C:54]4[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=4[NH:52][C:51]3=[O:61])[CH2:48][CH2:49]2)=[O:33])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 60 °C

Procedure

Triethylamine (50 μL, 0.358 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 (60 mg, 0.143 mmol) and 1,1′-carbonyldiimidazole (41 mg, 0.25 mmol) in tetrahydrofuran (3 mL) at 0° C. After 25 min, the hydrochloride salt of 3-piperidin-4-yl-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one (40 mg, 0.143 mmol) and dichloromethane (3 mL) were added and the mixture was heated to 60° C. After 16 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 (53 mg). MS 618.2572 (M+1).

Workup

waitAfter 16 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-1e4f2fc52ed444ed9921ba36c87a8e84
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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