2,4,6-Trimethylpyridine → HCID 131725787, compound

HRID 1828774Notes

Reaction equation

HRID 1828774 reaction equation
N1CC[CH2:4][CH2:3][CH2:2]1.[C:7]([NH:24][CH2:25][C:26]([OH:28])=[O:27])([O:9][CH2:10][CH:11]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:53][C:54]1[CH:59]=[C:58]([CH3:60])[N:57]=[C:56](C)[CH:55]=1>CN(C=O)C>[NH:24]([C:7]([O:9][CH2:10][CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:8])[CH2:25][C:26]([OH:28])=[O:27].[CH2:56]1[C:55]2[C:54](=[CH:53][CH:2]=[CH:3][CH:4]=2)[CH2:59][CH:58]([CH2:60][C:7]([OH:9])=[O:8])[NH:57]1

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 8082PiperidineHCID 93124Fmoc-Gly-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 131725787HCID 131725787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.072 mmol of A is washed with DMF (1×2 ml). The compound is subsequently deprotected twice using 20% of piperidine in DMF (2×2 ml), firstly for 5 minutes and then for 15 minutes, and washed with DMF (6×2 ml). An approximately 0.1M solution of 2.5 equivalents (based on the resin loading, 0.18 mmol) of Fmoc-glycine, 2.4 equivalents (0.17 mmol) of HATU and 30 equivalents (2.16 mmol) of sym-collidine in dry DMF is added to the resin-bound free amine, and the mixture is shaken at room temperature for 90 minutes. The reaction is terminated by washing in DMF (6×2 ml).

Workup

  1. waitfor 15 minutes
  2. washwashed with DMF (6×2 ml)
  3. customThe reaction is terminated
  4. washby washing in DMF (6×2 ml)

Sources & evidence

ORD record
ord-5b93c134447440dbad9b352b32e28602
Source dataset
uspto-grants-2006_06
Patent number
US07060707B2

Reaction notes

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