N,N-Dimethylglycine → HCID 10951763, compound

HRID 488766Notes

Reaction equation

HRID 488766 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C@H:7]([C:12]([NH:14][C@H:15]([CH2:19][N:20]3[CH2:25][CH2:24][C@:23]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=4)([CH3:26])[C@@H:22]([CH3:34])[CH2:21]3)[CH:16]([CH3:18])[CH3:17])=[O:13])[NH:8][CH2:9]2)=[CH:4][CH:3]=1.[CH3:35][N:36]([CH3:41])[CH2:37][C:38](O)=[O:39]>>[CH3:35][N:36]([CH3:41])[CH2:37][C:38]([N:8]1[C@@H:7]([C:12]([NH:14][C@H:15]([CH2:19][N:20]2[CH2:25][CH2:24][C@:23]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=3)([CH3:26])[C@@H:22]([CH3:34])[CH2:21]2)[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:6][C:5]2[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:9]1)=[O:39]

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 9956146JDTic

Product 1

HCID 10951763HCID 10951763, compoundYield 86%

Procedure

(3R)-7-Hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (14, 0.100 g, 0.285 mmol) was coupled to N,N-dimethylglycine as described above to yield crude product which was purified by flash chromatography (50% (CHCl3:MeOH:NH4OH, 80:18:2) in CHCl3) to afford (3R)-2-(N,N-dimethylglycyl)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (17, 0.101 g, 86%) as a white foam. LRMS (ES) m/z 551.4 (M+H)+.

Workup

  1. customto yield crude product which
  2. customwas purified by flash chromatography (50% (CHCl3:MeOH:NH4OH, 80:18:2) in CHCl3)

Sources & evidence

ORD record
ord-1167529358ad4a23b0304f9edfd7a27b
Source dataset
uspto-grants-2005_12
Patent number
US06974824B2

Reaction notes

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