Ammonia → HCID 66774989, compound

HRID 1256212Notes

Reaction equation

CN(C)S([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:19]#[N:20])=[CH:13][C:12]=3[C:11]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])=[N:10][C:9]=2[CH:8]=[N:7]1)(=O)=O.C(O)(C(F)(F)F)=O.N>C(Cl)Cl.O>[F:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([F:28])[C:21]=1[C:11]1[C:12]2[CH:13]=[C:14]([C:19]#[N:20])[CH:15]=[CH:16][C:17]=2[C:18]2[NH:6][N:7]=[CH:8][C:9]=2[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 250 ml round-bottomed flask is charged with 4 g of a mixture of the regioisomers of 7-cyano-5-(2,6-difluorophenyl)pyrazolo[4,3-c]isoquinoline-1-sulphonic acid dimethylamide in 160 ml of DCM. After cooling to 0° C. using an ice bath, 108 ml of TFA are added and the mixture is stirred at RT for 6 h. The mixture is concentrated under RP and the solid obtained is taken up in 600 ml of water, and 50 ml of 0.75 M ammonia solution are added. The aqueous phase is extracted with 3 times 150 ml of AcOEt. The organic extracts are combined, washed with saturated NaCl solution and then dried over MgSO4. Concentration of the AcOEt under RP gives 2.6 g of 5-(2,6-difluorophenyl)-1H-pyrazolo[4,3-c]isoquinoline-7-carbonitrile (beige solid). MS (E/I): m/z=306 (M+); 1H NMR: 7.38 (t, J=8.0 Hz, 2H); 7.72 (m, 1H); 8.24 (broad s, 1H); 8.34 (dd, J=1.5 and 8.5 Hz, 1H); 8.59 (s, 1H); 8.70 (d, J=8.5 Hz, 1H); 14.5 (very broad m, 1H).

Workup

concentrationThe mixture is concentrated under RP
customthe solid obtained
extractionThe aqueous phase is extracted with 3 times 150 ml of AcOEt
washwashed with saturated NaCl solution
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-48a6e9c647e6480cadf287a23f23d66e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461175B2

Reaction notes

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