Methylamine → HCID 67148753, compound

HRID 2428152Notes

Reaction equation

ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].C[CH2:15][N:16]([CH:20](C)C)C(C)C.[C:23]([O:27][C:28](=[O:43])[N:29]([CH2:33][C:34]1[CH:39]=[C:38]([CH2:40][OH:41])[CH:37]=[CH:36][C:35]=1[Cl:42])[CH:30]1[CH2:32][CH2:31]1)([CH3:26])([CH3:25])[CH3:24].CN>CC#N>[C:23]([O:27][C:28](=[O:43])[N:29]([CH2:33][C:34]1[CH:39]=[C:38]([CH2:40][O:41][C:15](=[O:3])[NH:16][CH3:20])[CH:37]=[CH:36][C:35]=1[Cl:42])[CH:30]1[CH2:31][CH2:32]1)([CH3:26])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

4-Nitrophenyl chloroformate (5.08 g, 24.4 mmol) and DIPEA (8.37 mL, 48.9 mmol) were added to a sol. of (2-chloro-5-hydroxymethyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (3.05 g, 9.78 mmol) in CH3CN (50 mL). The mixture was stirred at 60° C. for 20 h, and was allowed to cool to rt. MeNH2 (2M in THF, 49.0 mL, 98.0 mmol) was added, and the mixture was stirred at rt for 4 h. The mixture was partitioned between CH2Cl2 and water. The org. layer was washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/Et2O 9:1) yielded the title compound (2.67 g, 74%). LC-MS: tR=1.01 min; ES+: 313.37.

Workup

temperatureto cool to rt
stirringthe mixture was stirred at rt for 4 h
customThe mixture was partitioned between CH2Cl2 and water
washlayer was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the crude by FC (CH2Cl2/Et2O 9:1)

Sources & evidence

ORD record: ord-90fd978df4424836b79c0e8872528630
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968720B2

Reaction notes

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