Dimethylformamide → HCID 68591547, compound

HRID 736932Notes

Reaction equation

HRID 736932 reaction equation
[NH2:1][C@H: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(C(C)C)C(C)C)C.[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:42][CH2:41][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[NH:38][C:37]2=[O:47])[CH2:32][CH2:31]1.CN([CH:51]=[O:52])C>C1COCC1>[NH2:19][C:12]1[C:13]([C:15]([F:17])([F:18])[F:16])=[CH:14][C:9]([CH2:8][C@@H:2]([NH:1][C:51]([N:30]2[CH2:31][CH2:32][CH:33]([N:36]3[CH2:42][CH2:41][C:40]4[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=4[NH:38][C:37]3=[O:47])[CH2:34][CH2:35]2)=[O:52])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:10][C:11]=1[Cl:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 68591454HCID 68591454, compound

Product 1

HCID 68591547HCID 68591547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1.8 g (11.0 mmol) CDT were added to a solution of 3.2 g (10.2 mmol) of ethyl (R)-2-amino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionate and 1.8 mL (10.3 mmol) ethyldiisopropylamine in 150 mL THF cooled to 0° C. and the reaction mixture was stirred for 45 min at this temperature and after removal of the ice bath stirred for a further 30 min. Then 2.5 g (10.2 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one suspended in 50 mL THF were added. 40 mL DMF were added to the reaction solution and this was stirred for 2 h at 80° C. It was evaporated down i.vac., combined with 200 mL EtOAc and 200 mL 10% citric acid solution, the organic phase was separated off, extracted with 150 mL NaHCO3 solution and dried over Na2SO4. After elimination of the desiccant and solvent the desired product was obtained.

Workup

  1. customafter removal of the ice bath
  2. stirringstirred for a further 30 min
  3. additionwere added
  4. stirringthis was stirred for 2 h at 80° C
  5. customIt was evaporated down i.vac
  6. customthe organic phase was separated off
  7. extractionextracted with 150 mL NaHCO3 solution
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-62e6d74260734c91b97dbebf82fe58a7
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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