Benzoyl chloride → HCID 178429303, compound

HRID 2235475Notes

Reaction equation

HRID 2235475 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:5]([N:21]=1)=[CH:6][C:7]1[C:8]([CH3:20])([CH3:19])[C:9](=[O:18])[N:10]([CH2:13][CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:11]=1[CH:12]=2.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(CC)CC>C1COCC1.C(Cl)Cl>[CH:15]1([CH2:14][CH2:13][N:10]2[C:11]3[CH:12]=[C:4]4[NH:3][C:2]([NH:1][C:22](=[O:29])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[N:21][C:5]4=[CH:6][C:7]=3[C:8]([CH3:19])([CH3:20])[C:9]2=[O:18])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178429304HCID 178429304, compound

Product 1

HCID 178429303HCID 178429303, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of D8 (120 mg), benzoic acid chloride (87 μl), NEt3 (150 μl) in THF (1 ml) and CH2Cl2 (3 ml) is stirred at RT for 3 h. After evaporation EtOAc is added and the organic phase is washed with saturated NaHCO3 solution and brine, dried over MgSO4 and evaporated again. The residue is purified by preparative RP-HPLC to give the desired compound (13.4 mg).

Workup

  1. customAfter evaporation EtOAc
  2. additionis added
  3. washthe organic phase is washed with saturated NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated again
  6. customThe residue is purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-e886a695be5f4ad2b99ff11dc6469a1c
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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