Methylamine → HCID 11255366, compound

HRID 2109073Notes

Reaction equation

HRID 2109073 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:10][C:11]([OH:13])=O)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[N:2].[NH:22]=[C:23]=N.CN>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:10][C:11]([NH:22][CH3:23])=[O:13])=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[N:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 160435Carbodiimide2×HCID 11369986N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycine

Product 1

HCID 11255366HCID 11255366, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropyl-methyl)glycine (0.148 g, 0.5 mmol), and resin bounded carbodiimide (PS-Carbodiimide) (1.0 g, 1.26 mmol/g) was shaken in CH2Cl2 (15 mL) for 30 min, then methylamine (33% solution in water, 0.1 mL, 1 mmol) was added, and the mixture was shaken for another 12 h. The resin was filtered and washed with CH2Cl2 (2×10 mL). The resulting filtrate was concentrated under vacuum. The residue was purified via preparative HPLC to obtain 0.036 g (23%) of the title compound as a white foam: 1H NMR (400 MHz, CDCl3) δ 7.54 (d, J=8.5 Hz, 1H), 6.99 (bs, 1H), 6.89 (dd, J=8.8, 2.6 Hz, 1H), 6.28 (bs, 1H), 4.08 (s, 2H), 3.34 (d, J=6.6 Hz, 2H), 2.80 (d, J=4.7 Hz, 3H), 1.06 (m, 1H), 0.65 (m, 2H), 0.31 (m, 2H).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with CH2Cl2 (2×10 mL)
  3. concentrationThe resulting filtrate was concentrated under vacuum
  4. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-b47f165b4c6c4c74a222043e8863142f
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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