Trifluoroacetic acid → HCID 178492719, compound

HRID 1676635Notes

Reaction equation

HRID 1676635 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H: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]([O:43][CH3:44])[CH:17]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]1[CH2:13][CH2:12][C@H: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]([O:43][CH3:44])[CH:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178492720HCID 178492720, compound

Product 1

HCID 178492719HCID 178492719, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.046 g (0.07 mmole) of cis-{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-methoxy-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester (I-97), 2.25 mL of dichloromethane and 0.25 mL of trifluoroacetic acid was stirred for 1.5 hours and then concentrated under reduced pressure. The residue was diluted with methanol and neutralized with 1.0 M sodium hydroxide at 0 degrees. The methanol solution was purified by reverse phase silica gel chromatography, eluting with acetonitrile-water (gradient, 1:99-90:10) to give 0.0226 g of cis-N-(4-amino-cyclohexyl)-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-methoxy-benzamide (I-98).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with methanol and neutralized with 1.0 M sodium hydroxide at 0 degrees
  3. customThe methanol solution was purified by reverse phase silica gel chromatography
  4. washeluting with acetonitrile-water (gradient, 1:99-90:10)

Sources & evidence

ORD record
ord-aaa353f82f754de894909dc6fc9408aa
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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