Diisopropylethylamine → HCID 68738058, compound

HRID 240786Notes

Reaction equation

HRID 240786 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=3)[CH:9]=2)[N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:3]=1.C(N(C(C)C)CC)(C)C.[Br:39][CH2:40][C:41](Cl)=[O:42]>O1CCCC1>[CH2:16]([N:14]1[CH:15]=[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:3]=[C:2]3[NH:1][C:41](=[O:42])[CH2:40][Br:39])[N:12]=[N:13]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chloride2×HCID 68737159HCID 68737159, compound

Product 1

HCID 68738058HCID 68738058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Example 64A (500 mg, 1.28 mmol) in tetrahydrofuran (12 mL) was added diisopropylethylamine (0.22 mL, 1.28 mmol). The reaction mixture was stirred at ambient temperature for about 15 minutes then 2-bromoacetyl chloride (0.11 mL, 1.2 mmol) was added. The reaction mixture was stirred at ambient temperature for about 16 hours then additional 2-bromoacetyl chloride (0.11 mL, 1.2 mmol) was added. The reaction mixture was stirred for an additional 15 minutes then concentrated under reduced pressure to provide the title compound as a brown solid. This material was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for about 16 hours
  2. stirringThe reaction mixture was stirred for an additional 15 minutes
  3. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-af341b6b13804591bedd142ce03708a0
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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