Triethylamine → HCID 58020375, compound

HRID 1632079Notes

Reaction equation

HRID 1632079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH:15]([F:17])[F:16])=[CH:12][CH:11]=[C:10]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:25][NH2:26])=[N:23][CH:24]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36]>ClCCl>[C:38]1([O:37][C:35](=[O:36])[NH:26][CH2:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][C:10]3[CH:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[C:13]([O:14][CH:15]([F:16])[F:17])=[CH:12][CH:11]=3)=[CH:24][N:23]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 58020111HCID 58020111, compound

Product 1

HCID 58020375HCID 58020375, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In an 8 mL vial equipped with a stir bar was placed C-[5-(3′-chloro-6-difluoromethoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-methylamine (P-596, 115 mg, 0.307 mmol), dichloromethane (1.5 mL) and triethylamine (85.6 uL, 0.614 mmol). The solution was cooled to 0° C. and then phenyl chloroformate (57.8 uL, 0.461 mmol) was added and the mixture was stirred at 0° C. for 15 minutes. The reaction was quenched with water (3 mL) and then the organic portion was removed. The aqueous portion was extracted with dichloromethane (2 mL), the organic portions were combined, washed with brine (3 mL), dried (MgSO4), concentrated and purified by silica gel column chromatography utilizing 70% ethyl acetate/hexanes as the eluent to produce 78 mg of I-149 as a yellow viscous oil in 51% yield.

Workup

  1. customIn an 8 mL vial equipped with a stir bar
  2. customThe reaction was quenched with water (3 mL)
  3. customthe organic portion was removed
  4. extractionThe aqueous portion was extracted with dichloromethane (2 mL)
  5. washwashed with brine (3 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography
  9. customto produce 78 mg of I-149 as a yellow viscous oil in 51% yield

Sources & evidence

ORD record
ord-3ed2930a10c5474183c150cee692531b
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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