Triethylamine → HCID 68863999, compound

HRID 1725946Notes

Reaction equation

HRID 1725946 reaction equation
[CH2:1]([C:3]1[C:4]([O:23][CH3:24])=[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.[CH3:32][CH:33]1[N:38]([CH2:39][CH2:40][CH2:41][NH2:42])[CH2:37][CH2:36][CH2:35][CH2:34]1>C(#N)C>[CH2:1]([C:3]1[C:4]([O:23][CH3:24])=[C:5]([C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:42][CH2:41][CH2:40][CH2:39][N:38]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[CH3:32])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5202111-(3-Aminopropyl)-2-pipecolineHCID 68866351HCID 68866351, compound

Product 1

HCID 68863999HCID 68863999, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 318E (50 mg, 0.14 mmol), triethylamine (0.1 mL, 0.71 mmol), acetonitrile (1 mL) and 1-(3-aminopropyl)-2-pipecoline (177 mg, 1.1 mmol) was purged with argon, sealed in a vial and microwaved at 150° C. for 55 minutes. Purification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min provided the desired product. MS (ESI(+)) m/e 490 (M+H)+; (ESI(−)) m/e 488 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.24 (br s, 1H), 9.71 (br s, 1H), 7.58 (dd, 1H), 7.42 (t, 1H), 7.13 (d, 1H), 6.87 (dd, 1H), 6.67 (m, 2H), 6.05 (m, 1H), 3.69 (s, 3H), 3.36 (m, 2H), 3.12 (m, 2H), 3.05 (m, 2H), 2.88 (m, 1H), 2.54 (q, 2H), 1.86 (m, 4H), 1.64 (m, 2H), 1.43 (m, 2H), 1.20 (d, 3H), 1.10 (t, 3H).

Workup

  1. customsealed in a vial and
  2. custommicrowaved at 150° C. for 55 minutes
  3. customPurification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  4. customover 8 minutes
  5. custom(10 minute run time)

Sources & evidence

ORD record
ord-10877409805f4acfac73d9523c12ac71
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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