Water → 2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 524846Notes

Reaction equation

C(N(C(C)C)/[CH:5]=[C:6](\[F:9])/[CH:7]=O)(C)C.NC1C(C(ON2C3C=CC=CC=3N=N2)=O)=C2N=CC(CC#N)=CN2N=1.[NH2:38][C:39]1[C:43]([C:44]([NH:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][C:52]=2[N:53]2[CH2:58][CH2:57][N:56]([CH3:59])[CH2:55][CH2:54]2)=[O:45])=[C:42]([NH2:60])[NH:41][N:40]=1.O>CS(C)=O>[NH2:60][C:42]1[C:43]([C:44]([NH:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][C:52]=2[N:53]2[CH2:58][CH2:57][N:56]([CH3:59])[CH2:55][CH2:54]2)=[O:45])=[C:39]2[N:38]=[CH:5][C:6]([F:9])=[CH:7][N:40]2[N:41]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (Z)-3-(diisopropylamino)-2-fluoro-prop-2-enal (Tetrahedron Letters (1992), 33(3), 357-60) (22.81 mg, 0.1317 mmol), 4-methylbenzenesulfonic acid (Water (1)) (30.05 mg, 0.1580 mmol), 3,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide (50 mg, 0.1580 mmol) in DMSO (1 mL)/H2O (0.5 mL) was stirred at 140° C. for 25 min. The crude mixture was purified by Fractionlynx HPLC. The aqueous fractions were combined and lyophilised to yield 2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. (10 mg, 21%).

Workup

customThe crude mixture was purified by Fractionlynx HPLC

Sources & evidence

ORD record: ord-415311000d504200a33cf2f3d274d84b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340546B2

Reaction notes

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