4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide

HRID 2382122Notes

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

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (509 mg, 2.28 mmol) and 3-ethyl-5-fluoropyrrolo[2,3-b]pyridin-1-ylamine (340 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-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide (481 mg, 66%). MS: 383 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 11.95 (s, NH, 1H), 9.10 (s, 1H), 8.29 (s, 1H), 8.14 (d, 1H), 8.08 (d, 1H), 8.00 (m, 1H), 7.57 (s, 1H), 2.79 (s, 3H), 2.75 (q, 2H), 1.29 (t, 3H).

Workup

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

Sources & evidence

ORD record: ord-520df424142d49699577d2c802236e87
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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