Methylamine → HCID 21037779, compound

HRID 1791014Notes

Reaction equation

HRID 1791014 reaction equation
[C:1]1([S:7]([N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:27])([C:23]([F:26])([F:25])[F:24])[C:18]#[C:19][C:20](O)=[O:21])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN.Cl.[CH3:35][N:36](C)CCCN=C=NCC>C(Cl)Cl>[CH3:35][NH:36][C:20](=[O:21])[C:19]#[C:18][C:17]([C:14]1[CH:15]=[CH:16][C:11]([N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:12][CH:13]=1)([OH:27])[C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22042619HCID 22042619, compound

Product 1

HCID 21037779HCID 21037779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.2 g of 4-[4-(benzenesulfonyl-isobutyl-amino)-phenyl]-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid (see Example 69; 0.439 mmol) and 0.26 mL of methylamine (2M in THF) were combined in 3 mL of CH2Cl2 at rt. 0.1 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.527 mmol) was added. The resulting mixture was stirred at rt for 16 h. After addition of 80 mL of CH2Cl2 the resulting solution was washed with an aqueous solution of citric acid, a saturated aqueous solution of sodium bicarbonate and brine. The organic layers were dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica(EtOAc:hexanes, 1:1) to give the title compound. 1H NMR (400 MHz, CDCl3) δ 0.90 (m, 6H), 1.56 (m, 1H), 2.91 (d, J=5.0 Hz, 3H), 3.31 (m, 2H), 3.72 (br s, 1H), 6.26 (d, 5.0 Hz, 1H), 7.11 (d, J=8.7 Hz, 2H), 7.44–7.60 (m, 5H), 7.64 (d, J=8.7 Hz, 2H). Mass Spectrum (CI+) m/e=486 (M+18).

Workup

  1. washwas washed with an aqueous solution of citric acid
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica(EtOAc:hexanes, 1:1)

Sources & evidence

ORD record
ord-c3bc4ba7f6bb4a54a7d11f396736f8e8
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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