4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (2-cyclopropyl-5-fluoro-indol-1-yl)-amide

HRID 2382133Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (188 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-thiazol-2-yl-pyrimidine-5-carboxylic acid (2-cyclopropyl-5-fluoro-indol-1-yl)-amide (60 mg). MS: 394 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.26 (s, 1H), 8.15 (d, 1H), 8.08 (d, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 6.97 (m, 1H), 6.18 (s, 1H), 2.77 (s, 3H), 1.95 (m, 1H), 1.01 (m, 2H), 0.73 (m, 2H).

Workup

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

Sources & evidence

ORD record: ord-794aea4e6b374b44a6943a8df6706d4e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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