Dimethylformamide → Ethyl 3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionate

HRID 494749Notes

Reaction equation

HRID 494749 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([NH2:19])=[C:11]([Cl:20])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[NH:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:40][CH2:39][C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[NH:36][C:35]2=[O:45])[CH2:30][CH2:29]1.CN([CH:49]=[O:50])C>O>[NH2:19][C:12]1[C:13]([C:15]([F:17])([F:18])[F:16])=[CH:14][C:9]([CH2:8][CH:2]([NH:1][C:49]([N:28]2[CH2:29][CH2:30][CH:31]([N:34]3[CH2:40][CH2:39][C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[NH:36][C:35]3=[O:45])[CH2:32][CH2:33]2)=[O:50])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:10][C:11]=1[Cl:20]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 22184527Ethyl 2-amino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionate2×

Product 1

HCID 22184546Ethyl 3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4.15 g (23.04 mmol) CDT was added to a suspension of 8.00 g (23.04 mmol) ethyl 2-amino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionate (Intermediate product 58) and 16.0 mL (115.00 mmol) triethylamine in 100 mL DMF at 0° C. and the mixture was stirred for 1.5 hours at 0° C. A solution of 5.64 g (23.00 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one in 200 mL DMF was added and the mixture was heated to 100° C. for 2 hours. The reaction mixture was cooled to RT, diluted with 1.5 L water and stirred for a further 10 minutes. The precipitate formed was filtered off, washed with water and dried i. vac.

Workup

  1. temperaturethe mixture was heated to 100° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to RT
  3. stirringstirred for a further 10 minutes
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried i

Sources & evidence

ORD record
ord-0f08dae74b384c0c95bfa70330a3865d
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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