Triethylamine → HCID 66671934, compound

HRID 1913496Notes

Reaction equation

HRID 1913496 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@@H:18]([OH:21])[CH2:19][OH:20])=[CH:12][CH:11]=2)[C:5]([C:22]#[N:23])=[C:4]([S:24][CH2:25][C:26]2[N:27]=[C:28]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[O:29][CH:30]=2)[N:3]=1.Cl.N([CH2:41][C:42]([O:44][CH3:45])=[O:43])C.[CH2:46](N(CC)CC)C>C1COCC1>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:28]2[O:29][CH:30]=[C:26]([CH2:25][S:24][C:4]3[N:3]=[C:2]([N:1]([CH3:46])[CH2:41][C:42]([O:44][CH3:45])=[O:43])[C:7]([C:8]#[N:9])=[C:6]([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH2:17][C@@H:18]([OH:21])[CH2:19][OH:20])=[CH:14][CH:15]=4)[C:5]=3[C:22]#[N:23])[N:27]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 666718012-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(2S)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 66671934HCID 66671934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

451 mg (0.51 mmol) of the compound from Example 40A were dissolved in 7.8 ml of dry THF, and 141 mg (1.01 mmol) of methyl sarcosinate hydrochloride and 211 μl (1.52 mmol) of triethylamine were then added in succession. The reaction mixture was stirred at RT for 8 h. After removal of the solvent, the mixture was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customAfter removal of the solvent
  2. customthe mixture was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-a6e78e57f5c94eb5b59726c36c92a6d7
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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