Diethylethanolamine → HCID 11576769, compound

HRID 1725948Notes

Reaction equation

HRID 1725948 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9].Cl[C:26](Cl)([O:28][C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[CH2:37]([N:39]([CH2:43]C)[CH2:40][CH2:41]O)[CH3:38]>N1C=CC=CC=1>[CH2:37]([N:39]([CH2:40][CH3:41])[CH2:43][CH2:26][O:28][C:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9])=[O:35])[CH3:38]

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 94429TriphosgeneHCID 11573782HCID 11573782, compound

Product 1

HCID 11576769HCID 11576769, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of Example 294 (36.7 mg, 0.11 mmol), triphosgene (10.4 mg, 0.033 mmol), and pyridine (1 mL) was stirred for 3 hours at 70° C., treated with 2-(diethylamino)ethanol (70 μL, 0.53 mmol), stirred for 18 hours at 70° C., concentrated, and purified by Cl18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (4.5 mg, 9%). MS (ESI(+)) m/e 490 (M+H)+; MS (ESI(−)) m/e 488 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1H), 8.04 (d, 1H), 7.74 (dd, 1H), 7.64 (m, 1H), 7.24 (t, 1H), 6.97 (d, 1H), 6.65 (m, 1H), 4.40 (t, 2H), 3.20 (q, 6H), 2.56 (m, 4H), 1.66 (m, 4H), 1.20 (t, 6H).

Workup

  1. concentrationconcentrated
  2. custompurified by Cl18 reverse-phase

Sources & evidence

ORD record
ord-4a44519a07ee4668a9f4aa9e28aa7066
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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