Trifluoroacetic acid → HCID 58015151, compound

HRID 1676743Notes

Reaction equation

HRID 1676743 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:47])[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]([C:43]([F:46])([F:45])[F: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:36])([F:35])[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[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[O:47])=[CH:17][C:18]=4[C:43]([F:44])([F:45])[F:46])=[N:42][C:27]2=3)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58015115HCID 58015115, compound

Product 1

HCID 58015151HCID 58015151, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.0298 g (0.0446 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-trifluoromethyl-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (I-211) in 4 mL of dichloromethane was stirred with 2 mL of trifluoroacetic acid for 2 hours and then 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 0.0209 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)-N-piperidin-4-yl-3-trifluoromethyl-benzamide (I-212) 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-460748f26bcc4c1b9b568eb6867c956a
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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