Benzylamine → HCID 58404896, compound

HRID 1253530Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH3:18])[C:6]=12.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:19]([NH:26][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH3:18])[C:6]=12)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-bromo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (25.0 mg, 0.081 mmol), benzyl amine (12.0 mg, 0.011 mmol), tris[dibenzylideneacetone]dipalladium (0) (1.9 mg, 0.0020 mmol), and tert-butyl X-phos (3.5 mg, 8.1 mmol) were suspended in toluene (1.6 ml), sparged with argon for 3 minutes, then heated to 100° C. After 12 hours, the reaction mixture was concentrated. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give N-benzyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-amine 1H NMR (500 MHz, DMSO-d6) δ 8.23 (s, 1H); 8.17 (s, 1H); 7.91 (s, 1H); 7.38 (d, 2H); 7.29 (t, 2H); 7.25 (s, 1H); 7.20 (t, 1H); 6.44 (s, 1H); 4.92 (t, 1H); 4.23 (d, 2H); 3.93 (s, 3H); 3.83 (s, 3H). LRMS (ESI) calculated for C19H20N5O [M+H]+, 334.2; found 334.1.

Workup

customsparged with argon for 3 minutes
concentrationthe reaction mixture was concentrated
customThe residue was purified by preparative HPLC Reverse phase (C-18)
washeluting with acetonitrile/water+0.05% TFA

Sources & evidence

ORD record: ord-0cbb3556ec924a0bb32032733d0a1074
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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