Chloroacetyl chloride → HCID 66958132, compound

HRID 1364046Notes

Reaction equation

HRID 1364046 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:14][CH:13]=[CH:12][CH:11]=2>ClCCl>[ClH:1].[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[N:14][CH:13]=[CH:12][CH:11]=2)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 66958566HCID 66958566, compound

Product 1

HCID 66958132HCID 66958132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (5.00 mL, 63.4 mmol) was added dropwise to a 0° C. solution of tert-butyl 3-[(3-amino[1,5]naphthyridin-4-yl)amino]propylcarbamate (from Part D, approximately 57.6 mmol) in dichloromethane (230 mL). The reaction was allowed to warm to room temperature and was stirred for 1 hour. The solvent was removed under reduced pressure to afford tert-butyl 3-({3-[(chloroacetyl)amino][1,5]naphthyridin-4-yl}amino)propylcarbamate hydrochloride as a solid, all of which was used in the next step.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c92da5a059b048b182100972f07cd795
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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