Ethanolamine → HCID 86282039, compound

HRID 1052978Notes

Reaction equation

HRID 1052978 reaction equation
Cl[C:2]1([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]([CH3:17])=[N:13][O:14][C:15]=3[CH3:16])[CH:9]=2)[NH:4][C:3]1=[O:18].CCN(C(C)C)C(C)C.[NH2:33][CH2:34][CH2:35][OH:36]>C(Cl)Cl.O>[CH3:17][C:12]1[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3](=[O:18])[C:2]3([NH:33][CH2:34][CH2:35][OH:36])[C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)=[C:15]([CH3:16])[O:14][N:13]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 117668198HCID 117668198, compound

Product 1

HCID 86282039HCID 86282039, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

110 mg (0.33 mmol) Of 3-chloro-5-(3,5-dimethylisoxazol-4-yl)-3-(thiophen-3-yl)indolin-2-one and 220 mg (1.65 mmol) of DIPEA were dissolved in 25 ml of CH2Cl2. After the addition of 55 mg (0.65 mmol) of 2-aminoethanol, the reaction solution was stirred for 16 h at room temperature. Subsequently, the solution was diluted with water. The aqueous phase was extracted with CH2Cl2 (2×20 mL). The combined organic phases were washed with aqueous NaHCO3 and with water, dried and concentrated in vacuo. The resulting residue was purified by chromatography (eluent: CH2Cl2/MeOH=20/1) to give product (85 mg, 69.8%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ H 7.48-7.50m, 1H), 7.20-731 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 4.47 (t, J=5.6 Hz, 1H), 3.20-3.38 (m, 4H), 3.17 (d, J=5.3 Hz, 2H), 2.37 (s, 3H), 2.20 (s, 3H). MS (ESI) m/e [M+1]+ 370.

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 mL)
  2. washThe combined organic phases were washed with aqueous NaHCO3 and with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by chromatography (eluent: CH2Cl2/MeOH=20/1)

Sources & evidence

ORD record
ord-6722061bae054ce4aa9d38eca73c75ef
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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