Dichloromethane → (7-Bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid hydrochloride

HRID 1362082Notes

Reaction equation

HRID 1362082 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([Br:19])[CH:17]=[N:18][C:12]=2[NH:11][C:10](=[O:20])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:30]>>[ClH:30].[Br:19][C:16]1[CH:17]=[N:18][C:12]2[NH:11][C:10](=[O:20])[CH2:9][N:8]([CH2:7][C:6]([OH:21])=[O:5])[CH2:14][C:13]=2[CH:15]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59456902(7-Bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid tert-butyl ester

Product 1

HCID 66967063(7-Bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid hydrochlorideYield 98%

Procedure

A solution of (7-bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid tert-butyl ester (1.61 g, 4.52 mmol) in CH2Cl2 (20 mL) was treated with TFA (15 mL). After stirring at room temperature for 1 h, the solution was concentrated in vacuo. The resulting slurry was treated with anhydrous HCl (40 mL of a 4.0 M) and sonicated for 1.5 h, diluted with Et2O and stirred for 1 h. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. overnight to give the title compound (1.66 g, 98%) as a white solid: MS (ESI) m/e 300 (M+H)+.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe resulting slurry was treated with anhydrous HCl (40 mL of a 4.0 M) and
  3. customsonicated for 1.5 h
  4. additiondiluted with Et2O
  5. stirringstirred for 1 h
  6. customThe solid was isolated by filtration
  7. washwashed with Et2O
  8. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-cc3c3028d3b841ef8474e0e735d02f0f
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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