tert-butyl N-(4-aminobutyl)carbamate → HCID 67074748, compound

HRID 2042701Notes

Reaction equation

HRID 2042701 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([NH:11][C:12]3[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=4)[N:13]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:46]([O:45][C:44]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][NH:38][C:2]1[CH:3]=[C:4]([C:8]2([NH:11][C:12]3[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=4)[N:13]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)=[O:50])([CH3:49])([CH3:48])[CH3:47]

Participants

8

Reactant 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 67074285Tert-butyl 4-(4-(1-(3-bromophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Product 1

HCID 67074748HCID 67074748, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of tert-butyl 4-(4-(1-(3-bromophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (116 mg, 0.2 mmol),tert-butyl 4-aminobutylcarbamate (37.7 mg, 0.200 mmol), 2-(Di-t-butylphosphino)biphenyl (0.020 mmol), Pd2(dba)3 (18.31 mg, 0.020 mmol), K3PO4 (34.8 mg, 0.200 mmol) in a microwave tube in DME (Volume: 2 mL) was stirred for 3 h at 85° C. The reaction mixture was diluted with CH2Cl2, filtrated through a celite plug washing with CH2Cl2, concentrated to give a residue that was purified by Biotage eluting with 20%-50% ethyl acetate in hexane to give 38 mg (28%) of the desired product.

Workup

  1. filtrationfiltrated through a celite plug
  2. washwashing with CH2Cl2
  3. concentrationconcentrated
  4. customto give a residue that
  5. customwas purified by Biotage
  6. washeluting with 20%-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bee6d08c77b1468a8b7d702ce630eda3
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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