Triethylamine → HCID 68864536, compound

HRID 1725931Notes

Reaction equation

HRID 1725931 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:23])=[C:5]([C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2F)(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2].C(N(CC)CC)C.[CH2:31]([N:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][NH2:37])[CH3:32]>C(#N)C>[CH2:31]([N:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][NH:37][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:9]1[C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:23])[C:3]([CH2:1][CH3:2])=[CH:11][CH:10]=1)(=[O:15])=[O:14])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61011N,N-Diethyl-1,3-propanediamineHCID 68866305HCID 68866305, compound

Product 1

HCID 68864536HCID 68864536, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Example 230C (40 mg, 0.12 mmol), triethylamine (0.1 mL), and N,N-diethyl-1,3-propanediamine (0.1 mL) in acetonitrile (1.0 mL) was heated to 200° C. for 1 hour on a Personal Chemistry microwave instrument. The mixture was then purified by reverse phase HPLC to provide the desired product (5.8 mg, 10.8%). 1H NMR (DMSO-d6) δ 1.07 (t, 3H), 1.12 (t, 6H), 2.19 (s, 3H), 2.53 (q, 2H), 3.05-3.12 (m, 8H), 6.02 (br s, 1H), 6.62-6.66 (m, 2H), 6.84 (d, 1H), 7.03 (d, 1H), 7.40 (t, 1H), 7.52 (d, 1H), 8.98 (br s, 1H), 9.50 (br s, 1H); MS (ESI(+)) m/e 448 (M+H)+.

Workup

  1. customThe mixture was then purified by reverse phase HPLC

Sources & evidence

ORD record
ord-54ef4ee6f27442f9a741b2f402d83f09
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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