Pyrrolidine → N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxo-2-(pyrrolidin-1-yl)acetamide

HRID 1676237Notes

Reaction equation

HRID 1676237 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20]([O:22]CC)=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[CH:16][S:17][C:10]=12.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20](=[O:22])[N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[CH:16][S:17][C:10]=12

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 24983242Ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

Product 1

HCID 24983244N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxo-2-(pyrrolidin-1-yl)acetamideYield 86%

Procedure

Prepared from ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate (Example 2; 36 mg, 0.10 mmol) and pyrrolidine (36 mg, 0.50 mmol) according to the procedure for Example 3. The product was purified on a pre-packed Isoelute silica gel column (10 g silica), eluting with a gradient of 20% EtOAc/hexanes, 1:1 EtOAc/hexanes, 2:1 EtOAc/hexanes, and then neat EtOAc. The product was obtained as a white powder (33 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 8.52 (d, J=5 Hz, 1H), 7.87 (m, 1H), 7.75 (d, J=6 Hz, 1H), 7.58 (d, J=6 Hz, 1H), 7.37 (m, 1H), 7.26 (m, 1H), 6.52 (d, J=5 Hz, 1H), 4.09 (t, J=7 Hz, 2H), 3.63 (t, J=7 Hz, 2H), 2.02 (m, 2H), 1.91 (m, 2H). LRMS (ESI pos) m/e 386 (M+1). HPLC: 100% purity (220 nm).

Workup

  1. customThe product was purified on a pre-packed Isoelute silica gel column (10 g silica)
  2. washeluting with a gradient of 20% EtOAc/hexanes, 1:1 EtOAc/hexanes, 2:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-10e2c2df24e5423bb780ba589b641637
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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