Hydrochloric Acid → HCID 178509567, compound

HRID 872834Notes

Reaction equation

HRID 872834 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([Cl:18])[CH:11]=2)[CH:6]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[NH:29][N:28]=[C:27]([C:30](O)=[O:31])[CH:26]=2)[CH:20]=1.CCN(C(C)C)C(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl.Cl.CCOCC>>[Cl:18][C:12]1[CH:11]=[C:10]([C:7]2[CH:6]=[C:5]([CH2:4][CH2:3][NH:2][C:30]([C:27]3[CH:26]=[C:25]([C:21]4[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=4)[NH:29][N:28]=3)=[O:31])[O:9][N:8]=2)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10953452Ether hydrochlorideHCID 671683064-(5-(2-Aminoethyl)isoxazol-3-yl)-2-chlorobenzonitrile hydrochlorideHCID 178524127HCID 178524127, compound

Product 1

HCID 178509567HCID 178509567, compoundYield 47.4%

Procedure

The title compound was prepared from 4-(5-(2-aminoethyl)isoxazol-3-yl)-2-chlorobenzonitrile hydrochloride (0.080 g, 0.282 mmol), 5-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid (0.053 g, 0.282 mmol), DIPEA (0.196 ml, 1.126 mmol 1), HOBt hydrate (0.065 g, 0.422 mmol) and EDCI (0.081 g, 0.422 mmol) using the method of Example 274. The title compound was converted to HCl salt by treatment of 1 M HCl ether solution for 2 h affording 0.056 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): 3.15 (t, 2H), 3.66 (m, 2H), 7.16 (s, 1H), 7.42 (bs, 1H), 7.90 (m, 1H), 8.02 (d, 1H), 8.13 (d, 1H), 8.21 (s, 1H), 8.63 (d, 1H), 8.75 (d, 1H), 8.83 (bs, 1H), 9.19 (s, 1H).

Sources & evidence

ORD record
ord-8f3a416623b34446b2b4e6b82ccfe297
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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