Isopropylamine → N5-isopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine

HRID 2382773Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17]>C(O)CCC>[CH:16]([NH:19][C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 5-chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A7), 183.00 mg; 0.77 mmol; 1.00 eq.) and isopropylamine (664.58 μl; 7.74 mmol; 10.00 eq.) in n-butanol (1.50 mL) was heated at 120° C. for 1 h30 under MW irradiation. The reaction mixture was then concentrated under vacuum till dryness. The solid obtained was triturated in water/MTBE and filtered. The solid which precipitated in mother liquor was finally filtered, washed with water and dried under vacuum at 40° C. to give the title compound as an off-white solid (122 mg, 61%). HPLC, Rt: 2.64 min. (purity 86.5%). LC/MS, M+(ESI): 259.9, M−(ESI): 257.9.

Workup

concentrationThe reaction mixture was then concentrated under vacuum till dryness
customThe solid obtained
customwas triturated in water/MTBE
filtrationfiltered
customThe solid which precipitated in mother liquor
filtrationwas finally filtered
washwashed with water
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-6a2f52ad05c24ae7982123fa8c5556e1
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263595B2

Reaction notes

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