4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59200012, compound

HRID 2382132Notes

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.[CH:17]1([C:20]2[N:21]([NH2:30])[C:22]3[C:27]([CH:28]=2)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)[CH2:19][CH2:18]1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH:17]1([C:20]2[N:21]([NH:30][C:8]([C:7]3[C:2]([CH3:1])=[N:3][C:4]([C:11]4[N:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[N:5][CH:6]=3)=[O:10])[C:22]3[C:27]([CH:28]=2)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (184 mg, 0.85 mmol) and 2-cyclopropyl-5-fluoro-indol-1-ylamine (135 mg, 0.71 mmol) in DMF (3 mL) is stirred at 40° C. for 1 h. The mixture is treated with DMTMM (235 mg, 0.71 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-[2,2′]bipyrimidinyl-5-carboxylic acid (2-cyclopropyl-5-fluoro-indol-1-yl)-amide (35 mg, 13%). MS: 389 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 11.93 (s, NH, 1H), 9.31 (s, 1H), 9.06 (d, 2H), 7.70 (m, 1H), 7.42 (m, 1H), 7.26 (m, 1H), 6.97 (m, 1H), 6.16 (s, 1H), 2.79 (s, 3H), 1.97 (m, 1H), 1.01 (m, 2H), 0.74 (m, 2H).

Workup

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

Sources & evidence

ORD record: ord-2e3172efe3ec4ce48b76e116478c2eaf
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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