Dietylaminopropin → HCID 67347565, compound

HRID 1676268Notes

Reaction equation

I[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:3]=1.[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][C:23]#[CH:24])[CH3:20]>>[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][C:23]#[C:24][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:3]=1)[CH3:20]

Participants

Reactant 2

HCID 20010Dietylaminopropin

HCID 67347064HCID 67347064, compound

Product 1

HCID 67347565HCID 67347565, compound

Procedure

Prepared from 4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 72, Step A; 130 mg, 0.353 mmol), and N,N-diethylprop-2-yn-1-amine (58.9 mg, 0.530 mmol), according to the procedure for Example 6, Step B. The product was purified by Biotage 40S column (EtOAc). Product was an orange oil which crystallized upon standing (40 mg, 31%). 1H NMR (CDCl3, 400 MHz) δ 8.46 (d, J=5.5 Hz, 1H), 7.57 (s, 1H), 6.96 (d, J=9 Hz, 2H), 6.72 (d, J=9 Hz, 2H), 6.52 (d, J=5 Hz, 1H), 3.77 (s, 2H), 3.71 (s, 2H), 2.64 (q, J=7, 14 Hz, 4H), 1.13 (t, J=7 Hz, 6H). LRMS (ESI pos) m/e 352 (M+1).

Workup

customThe product was purified by Biotage 40S column (EtOAc)
customcrystallized

Sources & evidence

ORD record: ord-a4d2e19cd8284b61b28ae52bc9caa187
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003662B2

Reaction notes

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