4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59200003, compound

HRID 2382128Notes

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.[F:17][C:18]1[CH:19]=[C:20]2[CH:26]=[CH:25][N:24]([NH2:27])[C:21]2=[N:22][CH:23]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[F:17][C:18]1[CH:19]=[C:20]2[CH:26]=[CH:25][N:24]([NH:27][C:8]([C:7]3[C:2]([CH3:1])=[N:3][C:4]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[N:5][CH:6]=3)=[O:10])[C:21]2=[N:22][CH:23]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (440 mg, 2.28 mmol) and 5-fluoro-pyrrolo[2,3-b]pyridin-1-ylamine (288 mg, 1.9 mmol) in DMF (6 mL) is stirred at 40° C. for 1 h. The mixture is treated with DMTMM (524 mg, 1.9 mmol) and stirred at 40° C. for 1 h. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and stirred for 5 min. The precipitate is collected by filtration and dried in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide (343 mg, 52%). MS: 349 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.17 (s, 1H), 8.81 (d, 1H), 8.53 (d, 1H), 8.27 (s, 1H), 8.01 (m, 1H), 7.90 (m, 1H), 7.77 (d, 1H), 7.57 (m, 1H), 6.60 (d. 1H), 2.84 (s, 3H).

Workup

stirringstirred for 5 min
filtrationThe precipitate is collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-d15bd776b8c34b73804c29ec465f3d63
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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