2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → N-Methylbenzamide

HRID 1040924Notes

Reaction equation

O1C(N)CCOC2C=CC=CC1=2.ClC1N=C(N[C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([NH:25][CH3:26])=[O:24])C(Cl)=CN=1>C(O)(C(F)(F)F)=O>[CH3:26][NH:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:21]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A solution of 3,4-dihydro-2H-benz[b][1,4]dioxepin-ylamine (0.024 g, 0.00015 mol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methylbenzamide (0.04 g, 0.00013 mol) in TFA (0.5 mL) was evaporated and then heated to 115° C. for 15 min. Purification by ISCO chromatography gave 2-[5-chloro-2-(3,4-dihydro-2H-benzo[b]1,4]dioxepin-2-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide (0.036 g, 56%) vas a white solid. MP: 214-5° C.; 1H-NMR (DMSO-d6) δ 11.58 ((s, 1H), 9.36 (s, 1H), 8.74 (m, 2H), 8.20-1 (s, 1H), 7.74-6 (d, 1H), 7.50-2 (m, 1H), 7.42-8 (s, 1H), 7.14-6 (m, 2H), 6.86-8 (d, 1H), 4.05 (d, 2H), 4.09 (d, 2H), 2.81 (s, 3H), 2.07 (s, 2H); (LC/MS (ESI+): 426 (M+H).

Workup

customPurification by ISCO chromatography

Sources & evidence

ORD record: ord-ac7b4c65df834bd09021364a32f03534
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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