Cyclopropanemethanamine → N-(Cyclopropylmethyl)-4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzamide

HRID 1099078Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23]6[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=O)=[CH:25][CH:24]=6)[CH:21]=[N:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[Al](C)C.[CH:37]1([CH2:40][NH2:41])[CH2:39][CH2:38]1>C1(C)C=CC=CC=1.CO>[CH:37]1([CH2:40][NH:41][C:27](=[O:29])[C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:21]=[N:22][C:17]4[N:18]([C:14]([C:11]5([C:7]6[CH:6]=[C:5]7[C:10](=[CH:9][CH:8]=6)[N:1]=[CH:2][CH:3]=[CH:4]7)[CH2:12][CH2:13]5)=[N:15][N:16]=4)[N:19]=3)=[CH:32][CH:31]=2)[CH2:39][CH2:38]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate (15 mg, 0.036 mmol) in toluene (0.2 mL) was added 2.0 M of trimethylaluminum in toluene (27 μL) at RT followed by addition of cyclopropylmethylamine (5.0 mg, 0.071 mmol). The mixture was stirred at 70° C. overnight. After cooling the mixture was diluted with methanol, and filtered. The filtrate was purified by RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=462.4.

Workup

temperatureAfter cooling the mixture
filtrationfiltered
customThe filtrate was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-9c48b76cd19e44e090995d0e2b22d25c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143251B2

Reaction notes

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