Trifluoroacetic acid → HCID 58015146, compound

HRID 1676734Notes

Reaction equation

HRID 1676734 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:45])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:24]=[CH:25][C:26]4[N:32]([CH3:33])[C:31](=[O:34])[C:30]([F:36])([F:35])[CH2:29][N:28]([CH:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[C:27]=4[N:42]=3)=[C:18]([CH2:43][CH3:44])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:37]1([N:28]2[CH2:29][C:30]([F:35])([F:36])[C:31](=[O:34])[N:32]([CH3:33])[C:26]3[CH:25]=[N:24][C:23]([NH:22][C:19]4[CH:20]=[CH:21][C:16]([C:15]([NH:14][CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[O:45])=[CH:17][C:18]=4[CH2:43][CH3:44])=[N:42][C:27]2=3)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58015143HCID 58015143, compound

Product 1

HCID 58015146HCID 58015146, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.0447 g (0.0712 mmole) 4-[4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-ethyl-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (I-201) in 4 mL of dichloromethane was stirred with 2 mL of trifluoroacetic acid for 2 hours and concentrated under reduced pressure. The residue was dissolved in 80 mL of dichloromethane, washed with 15 mL of sodium carbonate solution, twice with 15 mL of brine and concentrated under reduced pressure. The residue was purified by reverse phase silica gel chromatography, eluting with water-acetonitrile (gradient, 90:10-0:100) to give 0.00269 g of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-ethyl-N-piperidin-4-yl-benzamide (I-202) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 80 mL of dichloromethane
  3. washwashed with 15 mL of sodium carbonate solution, twice with 15 mL of brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase silica gel chromatography
  6. washeluting with water-acetonitrile (gradient, 90:10-0:100)

Sources & evidence

ORD record
ord-4d18b9244c3841ee81a27efe3fea6a88
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

Loading…