Methanol → HCID 67250493, compound

HRID 1035313Notes

Reaction equation

HRID 1035313 reaction equation
C([N:8]1[CH2:18][CH2:17][N:16]2[C@@H:10]([CH2:11][CH2:12][O:13][C:14]3[C:22]([Br:23])=[CH:21][CH:20]=[CH:19][C:15]=32)[CH2:9]1)C1C=CC=CC=1.C(Cl)(=O)OCCCl.CO>ClC(Cl)C>[Br:23][C:22]1[C:14]2[O:13][CH2:12][CH2:11][C@H:10]3[CH2:9][NH:8][CH2:18][CH2:17][N:16]3[C:15]=2[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 123052-Chloroethyl chloroformateHCID 67250512HCID 67250512, compound

Product 1

HCID 67250493HCID 67250493, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of Example 236A (60 mg, 161 mmol) in dichloroethane (0.5 mL) was add chloroethyl carbonochloridate (39.1 mg, 0.273 mmol). The mixture was heated for 2 hours at 85° C. Methanol (2 mL) was added, and the mixture cooled to room temperature. The solution was concentrated and NaOH (1 M, aqueous) was added until pH=10. The product was extracted with ethyl acetate. Purification via flash chromatography (0-70% methanol/dichloromethane) afforded the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.12 (dd, J=7.93, 1.53 Hz, 1H), 6.81-6.98 (m, 2H), 4.27-4.38 (m, 1H), 4.13-4.21 (m, 1H), 3.02-3.15 (m, 3H), 2.89-2.99 (m, 1H), 2.76-2.88 (m, 2H), 2.64-2.75 (m, 1H), 1.83-1.98 (m, 2H); MS (DCI+) m/z 283 (M+H)+.

Workup

  1. temperaturethe mixture cooled to room temperature
  2. concentrationThe solution was concentrated
  3. additionNaOH (1 M, aqueous) was added until pH=10
  4. extractionThe product was extracted with ethyl acetate
  5. customPurification via flash chromatography (0-70% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c1816e2585774b4da723af654a1f3bb0
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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