Triethylamine → HCID 71533377, compound

HRID 2274946Notes

Reaction equation

[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]=2[C:7]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=[N:6]1.FC(F)(F)C([O-])=O.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[CH3:51][C:52]1([C:56](O)=[O:57])[CH2:55][O:54][CH2:53]1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[CH2:12][CH2:11][N:10]([C:56]([C:52]3([CH3:51])[CH2:55][O:54][CH2:53]3)=[O:57])[CH2:9][C:8]=2[C:7]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=[N:6]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 10° C. cold solution of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile, trifluoroacetate (7c) (0.055 g, 0.118 mmol) in N,N-dimethylformamide (2 ml) was added triethylamine (18 μl, 0.13 mmol), 1-hydroxybenzotriazole (17 mg, 0.124 mmol), 3-methyl-3-oxetane carboxylic acid (13.8 mg) and finally 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24 mg, 0.124 mmol). The mixture was allowed to warm to 25° C. and stirred for 16 h and purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 38 mg of 3-[1-(2,4-Difluoro-benzyl)-5-(3-methyl-oxetane-3-carbonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8a).

Workup

custompurified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-68a62d35edc74101aebb72d9b3ddacfc
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09127001B2

Reaction notes

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