Trifluoroacetic acid → HCID 67282603, compound

HRID 1910702Notes

Reaction equation

HRID 1910702 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:5]2[N:6]([CH3:37])[C:7](=[O:36])[CH:8]([CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][CH:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:17][CH:14]1[CH2:13][CH2:12][N:11]([C:10]2[C:4]3[CH:3]=[C:2]([Cl:1])[CH:39]=[CH:38][C:5]=3[N:6]([CH3:37])[C:7](=[O:36])[CH:8]([CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[N:9]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67471944HCID 67471944, compound

Product 1

HCID 67282603HCID 67282603, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,7-Dichloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (170 mg, 0.44 mmol) and tert-butyl piperidin-4-ylcarbamate (89 mg, 0.44 mmol) were coupled according to the corresponding procedure described in Example 14 to yield intermediate tert-butyl 1-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)piperidin-4-ylcarbamate. (85 mg, 35%). Tert-butyl 1-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)piperidin-4-ylcarbamate (85 mg, 0.16 mmol) was dissolved in dichloromethane (1 mL) and trifluoroacetic acid (1 mL) and stirred at ambient temperature for 2 hours. The solution was concentrated, redissolved in ethyl acetate and extracted into 1 M aqueous hydrochloric acid (3×10 mL). The extracts were neutralized with saturated sodium bicarbonate, extracted with dichloromethane (3×25 mL), then dried with sodium sulfate, filtered, and concentrated to yield 5-(4-aminopiperidin-1-yl)-7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (20 mg, 29% yield). MS (M+H)+447.2.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. extractionextracted into 1 M aqueous hydrochloric acid (3×10 mL)
  4. extractionextracted with dichloromethane (3×25 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-64bd894f411446dabf5f2c5def81537d
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

Loading…