Water → trans-N-(7-Chloro-1,2,3,4,10,14b-hexahydrodibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16192Notes

Reaction equation

HRID 16192 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32].O>CO>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:31](=[O:32])[C:30]([F:37])([F:36])[F:29])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 86599900trans-7-Chloro-1,2,3,4,10,14b-hexahydrodibenzo[b,f]pyrido[1,2-d][1,4]diazepine-1-amine

Product 1

HCID 86599899trans-N-(7-Chloro-1,2,3,4,10,14b-hexahydrodibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-7-chloro-1,2,3,4,10,14b-hexahydrodibenzo[b,f]pyrido[1,2-d][1,4]diazepine-1-amine (Structure 35 of scheme IX where X=N(H), R1=H, R2=H, R3=Cl, R4=H, R5=H, R10=H) (350 mg, 1.17 mmol) in methanol (22 mL) and triethylamine (0.7 mL) was added ethyl trifluoroacetate (1.5 mL). The reaction mixture was stirred at room temperature for 3 h. Water was added and the mixture was extracted with ethyl acetate (3×). The organic layers were washed with brine, dried (Na2SO4) and evaporated. After purification on silica with heptane/ethyl acetate 6:4 the title compound (90 mg, 19%) was obtained. Data: 1H-NMR (400 MHz, CDCl3) 1.69 (m, 1H), 1.86-1.94 (m, 2H), 2.11 (m, 1H), 2.99-3.09 (m, 2H), 4.47 (d, 1H), 4.86 (m, 1H), 5.79 (s, 1H, NH), 6.62 (d, J=8.2, 1H), 6.75 (dd, J=7.8, 1H), 6.89 (t, J=7.8, 1H), 6.91 (dd, J=8.2, J=2.7, 1H), 7.10 (d, J=2.7, 1H), 7.18 (t, J=7.8, 1H), 7.24 (d, J=7.8, 1H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customAfter purification on silica with heptane/ethyl acetate 6:4 the title compound (90 mg, 19%)
  6. customwas obtained

Sources & evidence

ORD record
ord-567820df0c254e20998e037a97defa7d
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

Loading…