Formamide → HCID 11544229, compound

HRID 2356977Notes

Reaction equation

HRID 2356977 reaction equation
Cl.[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15](NC)[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]([NH2:25])=O.[CH:26](OCCCC)=O>>[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:26][NH:25][CH3:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 11614Butyl FormateHCID 86606245HCID 86606245, compound

Product 1

HCID 11544229HCID 11544229, compoundYield 60%

Procedure

114 mg (0.376 mmol) of -(7-Benzenesulfonyl-chroman-4-yl)-methylamine HCl salt was dissolved in excess butyl formate and heated to reflux for 15 minutes. The resulting formamide was cooled to room temperature, concentrated, the residue dissloved in 3 mL THF and then reduced by adding 5 μL (1.5 eq., 0.563 mmol) of 10M BH3.DMS complex. The mixture was stirred for 1.5 h and quenched with methanol, partitioned between ethyl acetate and water, dried, concentrated and treated with 2 N HCl/EtOH and ether to provide 80 mg (60%) of (7-benzenesulfonyl-chroman-4-ylmethyl)-methyl-amine as the HCl salt, MS: 318 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 minutes
  3. concentrationconcentrated
  4. additionby adding 5 μL (1.5 eq., 0.563 mmol) of 10M BH3
  5. customquenched with methanol
  6. custompartitioned between ethyl acetate and water
  7. customdried
  8. concentrationconcentrated
  9. additiontreated with 2 N HCl/EtOH and ether

Sources & evidence

ORD record
ord-ccd2500a1f704892baca03cbecaaf1ec
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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