Dietylaminopropin → HCID 67349886, compound

HRID 1676266Notes

Reaction equation

HRID 1676266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[CH:30]=[C:31](I)[S:32][C:25]=34)=[CH:19][CH:18]=2)[C:9]([C:11]2([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[CH2:34]([N:36]([CH2:40][CH3:41])[CH2:37][C:38]#[CH:39])[CH3:35]>>[CH2:34]([N:36]([CH2:40][CH3:41])[CH2:37][C:38]#[C:39][C:31]1[S:32][C:25]2[C:26](=[N:27][CH:28]=[CH:29][C:24]=2[O:23][C:20]2[CH:21]=[CH:22][C:17]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:9]([C:11]3([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]3)=[O:10])=[CH:18][CH:19]=2)[CH:30]=1)[CH3:35]

Participants

3

Reactant 2

HCID 20010DietylaminopropinHCID 67349569HCID 67349569, compound

Product 1

HCID 67349886HCID 67349886, compoundYield 27.4%

Procedure

Prepared from N-(4-fluorophenyl)-N-(4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)cyclopropane-1,1-dicarboxamide (155 mg, 0.24 mmol) and N,N-diethylprop-2-yn-1-amine (24 mg, 0.21 mmol) according to the procedure for Example 6, Step B. The crude product was purified on a Horizon reverse phase using Biotage 12M C18 column. The crude was loaded to the samplet with EtOAc and dried under vacuum. Product eluted at 55-75% acetonitrile and was obtained as a white powder (32 mg, 24%). 1H NMR (CDCl3, 400 MHz) δ 9.58 (s, 1H), 8.94 (s, 1H), 8.46 (d, J=5 Hz, 1H), 7.61 (d, J=8.6 Hz, 2H), 7.54 (s, 1H), 7.47 (m, 2H), 7.14 (d, J=9.0 Hz, 2H), 7.03 (t, J=8.6 Hz, 2H), 6.55 (d, J=5 Hz, 1H), 3.70 (s, 2H), 2.65 (q, J=7, 14 Hz, 4H), 1.71 (m, 4H), 1.13 (t, J=7.4 Hz, 6H) (350 mg, 31%). LRMS (ESI pos) m/e 557 (M+1).

Workup

  1. customThe crude product was purified on a Horizon reverse phase
  2. customdried under vacuum
  3. washProduct eluted at 55-75% acetonitrile

Sources & evidence

ORD record
ord-853540457bfb4647a4388337310f6e10
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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