Trifluoroacetic acid → tert-Butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)piperidine-1-carboxylate

HRID 81951Notes

Reaction equation

HRID 81951 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C:19]4[C:24]([CH2:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=4[CH2:27][CH3:28])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[C:29]([N:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(O)(C(F)(F)F)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CN(C)C=O>[CH2:27]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH2:25][CH3:26])[C:19]=1[NH:18][C:16]([C:12]1[C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[N:11][C:2]([NH:1][CH:39]4[CH2:40][CH2:41][N:36]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:37][CH2:38]4)=[N:3][C:4]=3[C:5]=2[N:14]([CH3:15])[N:13]=1)=[O:17])[CH3:28]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 670756638-Amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 44555919tert-Butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)piperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1.0 g, 2.66 mmol) in dry dimethylformamide (20 mL), were added 1-Boc-4-piperidone (1.06 g mL, 5.32 mmol), CF3COOH (1.7 mL, 22.7 mmol) and NaBH(OAc)3 (1.12 g, 5.32 mmol). After 20 hours, NaOH 2N (12 mL, 24 mmol) was added dropwise to the mixture. The precipitate was filtered, washed with water and dried. The crude material was purified by flash chromatography on silica gel eluted with dichloromethane/methanol 97:3 to give the 1.2 g of to the pure title compound (80% yield).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customThe crude material was purified by flash chromatography on silica gel
  5. washeluted with dichloromethane/methanol 97:3

Sources & evidence

ORD record
ord-1c4f728ea8b24a8e94efc7edc2079012
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Reaction notes

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