HCID 58102934, compound → HCID 58103062, compound

HRID 389635Notes

Reaction equation

HRID 389635 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Cl[C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[N:32]([CH:33]5[CH2:35][CH2:34]5)[CH:31]=[N:30][N:29]=4)[CH:23]=3)=[O:20])[CH:14]=2)=[CH:9][N:8]=1>CN1C=CC=CC1.O1CCCC1>[CH:33]1([N:32]2[CH:31]=[N:30][N:29]=[C:28]2[C:24]2[CH:23]=[C:22]([NH:21][C:19](=[O:20])[C:15]3[CH:14]=[C:13]([C:10]4[CH:9]=[N:8][C:7]([CH:1]5[CH2:3][CH2:2]5)=[N:12][CH:11]=4)[CH:18]=[CH:17][N:16]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 2

HCID 58102934HCID 58102934, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 58103062HCID 58103062, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 125655021-Methyl-1,2-dihydropyridineSolvent

Procedure

Cyclopropyl magnesium bromide (0.5 M solution in tetrahydrofuran, 6.3 mL, 3 equiv) was added to a solution of 4-(2-chloropyrimidin-5-yl)-N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)picolinamide (440 mg, 1.06 mmol) and Fe(acac)3 (37 mg, 10 mol %) in N-methylpyridine (20 mL) and tetrahydrofuran (5 mL). After stirring for 5 minutes, the brown solution was quenched with 1 M hydrochloric acid (6 mL) and concentrated under reduced pressure at 70° C. The residue was purified by reverse-phase HPLC to give N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)-4-(2-cyclopropylpyrimidin-5-yl)picolinamide as a pale-yellow powder (200 mg, 45% yield). C24H21N7O. 424.1 (M+1). 1H NMR (DMSO) d 10.95 (s, 1H), 9.18 (s, 2H), 8.86 (d, J=5.2 Hz, 1H), 8.63 (s, 1H), 8.58 (s, 1H), 8.51 (d, J=1.2 Hz, 1H), 8.11 (dd, J=5.2, 2.0 Hz, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.55 (t, J=8.0 Hz, 1H), 3.66 (m, 1H), 2.32 (m, 1H), 1.10 (m, 6H), 0.95 (m, 2H).

Workup

  1. customthe brown solution was quenched with 1 M hydrochloric acid (6 mL)
  2. concentrationconcentrated under reduced pressure at 70° C
  3. customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-d9b75f42b40948b1b3075c54868e01fe
Source dataset
uspto-grants-2013_02
Patent number
US08378108B2

Reaction notes

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