Diisopropylethylamine → HCID 68738058, compound

HRID 1752573Notes

Reaction equation

HRID 1752573 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-d5f4c8f24a314a3e964e4c3a3c1ee1b1
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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