Trifluoroacetic acid → HCID 178514006, compound

HRID 591954Notes

Reaction equation

HRID 591954 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.C(OC([N:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH:38]=[C:37]([CH:39]=O)[CH:36]=[N:35]2)[CH2:30][CH2:29]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:39]([C:37]3[CH:36]=[N:35][N:34]([CH:31]4[CH2:32][CH2:33][NH:28][CH2:29][CH2:30]4)[CH:38]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86810415N-(N-BOC-Piperidino)pyrazole-4-carboxaldehydeHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178514006HCID 178514006, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 4-(4-formyl-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester were reacted in a similar fashion as for the synthesis of III. The resulting product was treated with 20 equivalents of trifluoroacetic acid in dichloromethane at 40° C. overnight. The solution was concentrated and neutralized to afford the title compound as a tan solid (64%). Mp. 203-5° C. 1H NMR (d-4 methanol): 8.27 (s, 1H), 8.07 (s, 1H), 7.89 (s, 1H), 6.42 (m, 1H), 6.37 (m, 1H), 5.32 (m, 1H), 4.87 (m, 3H), 4.44 (m, 1H), 3.33 (m, 2H), 3.25 (m, 2H), 2.98 (s, 1H), 2.90-2.72 (m, 4H), 2.36 (d, J=8 Hz, 1H), 2.20 (m, 2H), 2.04 (m, 2H), 1.57 (d, J=8 Hz, 1H). MS: 452.9 (M+H). HPLC retention time: 1.60 minutes (G Method).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-5fe8a56d2f734aee84145f418488d330
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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