Acetic Anhydride → HCID 70982587, compound

HRID 2283500Notes

Reaction equation

HRID 2283500 reaction equation
C(N(CC)C(C)C)(C)C.C(O[C:14](=[O:16])[CH3:15])(=O)C.[NH2:17][C@H:18]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][C:26]([C:29]3[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([NH:36][C:37]4[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][N:38]=4)[N:30]=3)=[CH:25][CH:24]=2)[CH2:19]1>C1COCC1>[CH3:35][C:33]1[CH:32]=[C:31]([NH:36][C:37]2[CH:42]=[C:41]([C:43]([F:44])([F:46])[F:45])[CH:40]=[CH:39][N:38]=2)[N:30]=[C:29]([C:26]2[CH:27]=[N:28][C:23]([N:20]3[CH2:21][CH2:22][C@H:18]([NH:17][C:14](=[O:16])[CH3:15])[CH2:19]3)=[CH:24][CH:25]=2)[CH:34]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86732001HCID 86732001, compound

Product 1

HCID 70982587HCID 70982587, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Diisopropylethylamine (0.032 mL, 0.181 mmol), acetic anhydride (6.26 μL, 0.066 mmol), 6′-[(3S)-3-aminopyrrolidin-1-yl]-4-methyl-N-[4-(trifluoromethyl)pyridin-2-yl]-2,3′-bipyridin-6-amine (Example 5, 25 mg, 0.060 mmol), and THF (1 mL) were added to a flask and stirred at room temperature for 16 hours. The crude solution was purified via reverse phase high pressure liquid chromatography to afford N-[(3S)-1-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)pyrrolidin-3-yl]acetamide. MS ESI calcd. for C23H24F3N6O [M+H]+ 457. found 457. 1H NMR (500 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.76 (s, 1H), 8.60 (s, 1H), 8.47 (d, J=5.0 Hz, 1H), 8.11 (m, 1H), 7.24 (s, 1H), 7.17 (d, J=5.0 Hz, 1H) 7.12 (s, 1H), 6.46 (d, J=8.8 Hz, 1H), 3.52-3.60 (m, 3H), 3.43 (m, 1H), 3.12 (m, 1H), 2.30 (s, 3H), 2.05 (s, 1H), 1.87-1.80 (m, 2H), 1.72 (s, 1H). rhSyk IC50=17 nM.

Workup

  1. customThe crude solution was purified via reverse phase high pressure liquid chromatography

Sources & evidence

ORD record
ord-275933a271744e5a991a0f28aef376c3
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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