tert-butyl N-[(4-aminophenyl)methyl]carbamate → HCID 178426946, compound

HRID 640970Notes

Reaction equation

HRID 640970 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[C:31]([O:35][C:36](=[O:46])[NH:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)([CH3:34])([CH3:33])[CH3:32]>C1COCC1>[C:31]([O:35][C:36](=[O:46])[NH:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12](=[O:13])[C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:15]=4)=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])=[CH:43][CH:44]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 178426964HCID 178426964, compound

Product 1

HCID 178426946HCID 178426946, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2 mL). To the resulting solution was added (4-Amino-benzyl)-carbamic acid tert-butyl ester (55.3 mg, 0.249 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture causing a black precipitate to form. The precipitate was vacuum filtered and the filtrate was then concentrated in vacuo and redissolved into ˜3 mL of EtOAc. Hexanes were added causing a yellow precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 48% (0.072 g, 0.119 mmol) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto form
  3. filtrationfiltered
  4. concentrationthe filtrate was then concentrated in vacuo
  5. dissolutionredissolved into ˜3 mL of EtOAc
  6. additionHexanes were added
  7. customto form
  8. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-24b85df0942b4e09b8ca05dc0622a366
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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