Acetic Acid → HCID 178437932, compound

HRID 1500404Notes

Reaction equation

C([O:5][C:6]([CH2:8][C:9]1[C:10]([CH2:27][CH3:28])=[N:11][N:12]([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][C:18]=2[F:26])[C:13]=1[CH2:14][CH3:15])=[O:7])(C)(C)C.C(N(C(C)C)CC)(C)C.[NH2:38][C:39]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][N:40]=1.C(O)(=O)C>CN(C)C=O>[CH2:27]([C:10]1[C:9]([CH2:8][C:6]([OH:5])=[O:7])=[C:13]([CH2:14][CH3:15])[N:12]([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]3[NH:38][C:39]4=[N:40][CH:41]=[CH:42][CH:43]=[C:44]4[N:45]=3)=[CH:19][C:18]=2[F:26])[N:11]=1)[CH3:28]

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred solution of 4-(4-tert-butoxycarbonylmethyl-3,5-diethylpyrazol-1-ylmethyl)-3-fluorobenzoic acid (19 mg) in dimethylformamide (2 ml) at room temperature is added diisopropylethylamine (50 μl). After 10 min, the solution is added to 2,3-diaminopyridine (7 mg). After 2 days, glacial acetic acid (2 ml) is added and the reaction is heated to 130° C. After 15 h, the reaction is allowed to cool to room temperature and concentrated in vacuo. The residue is dissolved in dichloromethane and trifluoroacetic acid (200 μl) and water (200 μl) are added. After 15 h, the reaction mixture is concentrated in vacuo. The residue is purified by HPLC to yield (3,5-diethyl-1-[2-fluoro-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzyl]-1H-pyrazol-4-yl)acetic acid (10 mg; [M+H]=429; HPLC retention time 1.34 min (Method A)).

Workup

waitAfter 2 days
waitAfter 15 h
temperatureto cool to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue is dissolved in dichloromethane
additiontrifluoroacetic acid (200 μl) and water (200 μl) are added
waitAfter 15 h
concentrationthe reaction mixture is concentrated in vacuo
customThe residue is purified by HPLC

Sources & evidence

ORD record: ord-3d239b85bd184c38a96e283914984637
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206164B2

Reaction notes

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