Dietylaminopropin → N-(3-chloro-4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 1676275Notes

Reaction equation

HRID 1676275 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:20]([C:22]2([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]2)=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16](I)[S:17][C:10]=12.[CH2:35]([N:37]([CH2:41][CH3:42])[CH2:38][C:39]#[CH:40])[CH3:36]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:19]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:20]([C:22]2([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]2)=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:40]#[C:39][CH2:38][N:37]([CH2:41][CH3:42])[CH2:35][CH3:36])[S:17][C:10]=12

Participants

3

Reactant 2

HCID 20010DietylaminopropinHCID 67349682N-(3-chloro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Product 1

HCID 67348683N-(3-chloro-4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamideYield 28.7%

Procedure

Prepared from N-(3-chloro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl) -N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (0.160 g, 0.132 mmol), and N, N-diethylprop-2-yn-1-amine (0.0132 g, 0.118 mmol) according to the procedure for Example 6, Step B. The product was purified by Horizon reverse phase using Biotage 12M C18 column. The crude was loaded to the samplet with EtOAc and dried under vacuum. The product was eluted with 55-75% acetonitrile in water and was obtained as a white powder (20 mg, 26%). 1H NMR (CDCl3, 400 MHz) δ 10.14 (s, 1H), 8.50 (s, 1H), 8.46 (d, J=5.5 Hz, 1H), 7.90 (s, 1H), 7.54 (s, 1H), 7.46 (m, 3H), 7.20 (d, J=8.6 Hz, 1H), 7.05 (t, J=8.8 Hz, 2H), 6.42 (d, J=5.5 Hz, 1H), 3.71 (s, 2H), 2.65 (q, J=7, 14 Hz, 4H), 1.77 (m, 4H), 1.13 (t, J=7.2 Hz, 6H). LRMS (ESI pos) m/e 591 (M+1).

Workup

  1. customThe product was purified by Horizon reverse phase
  2. customdried under vacuum
  3. washThe product was eluted with 55-75% acetonitrile in water

Sources & evidence

ORD record
ord-2d45f1b5bf50496fba04f2539d77b6f0
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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