Dichloromethane → (E)-3-[4-(2-Morpholin-4-yl-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid hydrochloride

HRID 1362078Notes

Reaction equation

HRID 1362078 reaction equation
C([O:5][C:6](=[O:29])/[CH:7]=[CH:8]/[C:9]1[CH:28]=[N:27][C:12]2[NH:13][C:14](=[O:26])[CH2:15][N:16]([CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:38]>>[ClH:38].[N:20]1([CH2:19][CH2:18][N:16]2[CH2:17][C:11]3[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:29])=[O:5])[CH:28]=[N:27][C:12]=3[NH:13][C:14](=[O:26])[CH2:15]2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59456904(E)-3-[4-(2-Morpholin-4-yl-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester

Product 1

HCID 66967154(E)-3-[4-(2-Morpholin-4-yl-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid hydrochlorideYield 96%

Procedure

A solution of (E)-3-[4-(2-morpholin-4-yl-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester (92 mg, 0.23 mmol) in CH2Cl2 (2 mL) was treated with TFA (2 mL). After stirring at room temperature for 30 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl (4 mL of a 4.0 M solution in dioxane, 16 mmol) and then sonicated for 15 min. The mixture was diluted with Et2O and sonicated for 10 min. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. for 4.5 hr to give the title compound (0.10 g, 96%) as an off-white solid: MS (ESI) m/e 347 (M+H)+.

Workup

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl (4 mL of a 4.0 M solution in dioxane, 16 mmol) and
  3. customthen sonicated for 15 min
  4. additionThe mixture was diluted with Et2O
  5. customsonicated for 10 min
  6. customThe solid was isolated by filtration
  7. washwashed with Et2O
  8. customdried under vacuum at 50° C. for 4.5 hr

Sources & evidence

ORD record
ord-ed8c825313404d86bb7d0373458041e8
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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