Triethylamine → HCID 68866168, compound

HRID 1725973Notes

Reaction equation

HRID 1725973 reaction equation
[CH2:1]([O:3][C:4]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[C:9]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2F)(=[O:18])=[O:17])[C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].C(N(CC)CC)C.[CH3:33][N:34]1[CH2:38][CH2:37][CH2:36][CH:35]1[CH2:39][CH2:40][NH2:41]>C(#N)C>[CH2:1]([O:3][C:4]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[C:9]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:41][CH2:40][CH2:39][CH:35]2[CH2:36][CH2:37][CH2:38][N:34]2[CH3:33])(=[O:18])=[O:17])[C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 68863989HCID 68863989, compound

Product 1

HCID 68866168HCID 68866168, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Example 385I (120 mg, 0.33 mmol), triethylamine (0.24 mL) and N-methyl-2-(2′-aminoethyl)pyrrolidine (217 mg, 1.7 mmol) in acetonitrile (3 mL) was heated to 120° C. in a sealed vial for 2 days, concentrated, and purified using a reverse phase HPLC, giving the desired product, 79 mg, 50.3%. 1H NMR (DMSO-d6) δ 1.08 (t, 3H), 1.28 (t, 3H), 1.60-1.70 (m, 1H), 1.80-2.00 (m, 3H), 2.12-2.30 (m, 2H), 2.53 (q, 2H), 2.68 (s, 3H), 2.90-3.04 (m, 1H), 3.20-3.32 (m, 3H), 3.50-3.60 (m, 1H), 3.90 (q, 2H), 5.98 (br s, 1H), 6.60 (d, 1H), 6.68 (t, 1H), 6.85 (d, 1H), 7.15 (d, 1H), 7.40 (t, 1H), 7.58 (d, 1H), 9.68 (s, 1H), 10.48 (br s, 1H); MS (ESI(+)) m/e 476 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified

Sources & evidence

ORD record
ord-4f3b0bc823804a83bf49455dda152d48
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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