Methanesulfonamide → HCID 58109373, compound

HRID 2037472Notes

Reaction equation

HRID 2037472 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][C:32](O)=[O:33])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:35])[CH3:16])=[CH:11][CH:10]=1.[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][C:32]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:33])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:35])[CH3:16])=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 72879MethanesulfonamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58109119HCID 58109119, compound

Product 1

HCID 58109373HCID 58109373, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acid (60 mg, 0.13 mmol), methanesulfonamide (24 mg, 0.26 mmol), HOBt (53 mg, 0.39 mmol), EDCl (75 mg, 0.39 mmol) and DIEA (1 mL) in CH2Cl2 was stirred at rt overnight. The solvent was removed to give the crude product. It was purified by preparative HPLC to give 3-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)-N-(methylsulfonyl)propanamide (7 mg, 10%). 1H NMR (CDCl3): 1.50 (m, 3H), 2.21 (m, 6H), 2.54 (m, 1H), 2.93 (m, 1H), 3.15 (s, 3H), 5.59 (m, 1H), 6.83 (m, 2H), 6.98 (m, 4H), 7.18 (m, 2H), 7.24 (m, 3H), 9.58 (s, 1H). LC-MS Method 3, tR=1.26 min, m/z=561.

Workup

  1. customThe solvent was removed
  2. customto give the crude product
  3. customIt was purified by preparative HPLC

Sources & evidence

ORD record
ord-5ed8f2f2de134806835846a4f3d2f9d1
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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