Cyclopropanemethanamine → HCID 178512089, compound

HRID 2189491Notes

Reaction equation

FC(F)(F)C1C=C(S([N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[N:19]=3)[CH2:14][CH2:13]2)(=O)=O)C=CC=1.[F:28][C:29]([F:42])([F:41])[O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.[CH:43]1([CH2:46][NH2:47])[CH2:45][CH2:44]1>C(O)C>[CH:43]1([CH2:46][NH:47][C:24]([C:20]2[N:19]=[C:18]([C:15]3[CH2:14][CH2:13][N:12]([S:37]([C:34]4[CH:35]=[CH:36][C:31]([O:30][C:29]([F:42])([F:41])[F:28])=[CH:32][CH:33]=4)(=[O:39])=[O:38])[CH2:17][CH:16]=3)[CH:23]=[CH:22][CH:21]=2)=[NH:25])[CH2:45][CH2:44]1

Participants

Conditions

Temperature: 55 °C

Procedure

N-Cyclopropylmethyl-1′-(4-trifluoromethoxybenzenesulfonyl)-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-6-carboxamidine (34) was synthesized as follows. Compound 33 was prepared according to the procedure described above for preparing compound 32 using 4-(trifluoromethoxy)benzenesulfonyl chloride instead of 3-trifluoromethylbenzenesulfonyl chloride. To a solution of compound 33 (154 mg, 0.37 mmol) in ethanol was added cyclopropylmethylamine (52 mg, 0.75 mmol) and the resulting solution was heated at 55° C. for 12 hours. The mixture was purified, without an aqueous work-up, on CombiFlash® and further purified by Prep-TLC to obtain the title compound 34 (7 mg, yield 4%). 1H NMR (400 MHz, CD3OD): δ 7.97-7.85 (m, 4H), 7.77 (d, 1H, J=8 Hz), 7.43 (d, 2H, J=8.8 Hz), 6.76 (m, 1H), 3.81 (m, 2H), 3.32 (m, 4H), 2.71 (m, 2H), 1.14 (m, 1H), 0.58 (m, 2H), 0.31 (m, 2H); MS: 481 (M+H+).

Workup

customN-Cyclopropylmethyl-1′-(4-trifluoromethoxybenzenesulfonyl)-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-6-carboxamidine (34) was synthesized
customThe mixture was purified, without an aqueous work-up, on CombiFlash®
customfurther purified by Prep-TLC

Sources & evidence

ORD record: ord-65e90c4db53d45c5a01efc92f01f87e2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324249B2

Reaction notes

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