1,2-Dichloroethane → HCID 71285201, compound

HRID 1481805Notes

Reaction equation

HRID 1481805 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[C:32]3[C:28]([CH:29]=[C:30]([CH:34]=O)[NH:31]3)=[CH:27][CH:26]=2)[C:22]([CH2:36][CH3:37])=[C:21]([O:38][CH2:39]C2C=CC=CC=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46][NH:47][CH3:48].[CH3:49][C:50](O)=O.[C:53](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:54].[Na+].Cl[CH2:68][CH2:69]Cl>>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[C:32]3[C:28]([CH:29]=[C:30]([CH2:34][N:47]([CH3:48])[CH3:46])[NH:31]3)=[CH:27][CH:26]=2)[C:22]([CH2:36][CH3:37])=[C:21]([O:38][CH2:39][C:69]2[CH:68]=[CH:49][CH:50]=[CH:54][CH:53]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 89422949HCID 89422949, compound

Product 1

HCID 71285201HCID 71285201, compoundYield 86%

Procedure

The product from Step 6 (40 mg, 0.067 mmol) was combined with dimethylamine (0.13 mmol, 2 M in THF) and AcOH (7.5 μL, 0.13 mmol) in 1,2-dichloroethane (1 mL). The mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (28 mg, 0.13 mmol) was added to the solution. The mixture stirred 30 min at room temperature, and then was partitioned between CH2Cl2 (4 mL) and aqueous 1 M K2CO3 (4 mL). The organic layer was loaded onto silica gel and eluted with 0-10% MeOH in CH2Cl2 to afford the title compound (36 mg, 86%). LC-MS 626.6 [M+H]+, RT 1.26 min.

Workup

  1. stirringThe mixture stirred 30 min at room temperature
  2. customwas partitioned between CH2Cl2 (4 mL) and aqueous 1 M K2CO3 (4 mL)
  3. washeluted with 0-10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6eacf4f99841463ba68e4557a73a54ed
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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