Diisopropylethylamine → HCID 86638352, compound

HRID 1516879Notes

Reaction equation

HRID 1516879 reaction equation
O.[OH:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1.[F:12][P-:13]([F:18])([F:17])([F:16])([F:15])[F:14].[N:19]1([O:28][C:29]([N:33]([CH3:35])[CH3:34])=[N+:30]([CH3:32])[CH3:31])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[N:20]1.[CH:36]([N:39]([CH2:43][CH3:44])[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>CN(C)C=O>[CH3:35][N:33]([C:29]([O:28][N:19]1[N:20]=[N:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]1=2)=[N+:30]([CH3:31])[CH3:32])[CH3:34].[F:12][P-:13]([F:18])([F:17])([F:16])([F:15])[F:14].[CH:10]1[CH:9]=[CH:8][C:7]2[N:3]([OH:2])[N:4]=[N:5][C:6]=2[CH:11]=1.[CH3:44][CH2:43][N:39]([CH:40]([CH3:42])[CH3:41])[CH:36]([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 86638352HCID 86638352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The scaffold (3 eq), 1-hydroxybenzotriazole hydrate (3 eq), and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (3 eq) were dissolved in N,N-dimethylformamide (2 mL) and added to the resin. N,N-diisopropylethylamine (9 eq) was added and the reaction mixture was agitated for 3 hours at room temperature, however, some scaffolds were agitated for 18 hours. The reagents were removed from the resin and the resin was washed with dichloromethane (5 mL), methanol (5 mL), and N,N-dimethylformamide (5 mL). A Kaiser test was performed and, if negative (i.e., no free amine present), the resin was deemed suitable for further transformation.

Workup

  1. additionadded to the resin
  2. stirringhowever, some scaffolds were agitated for 18 hours
  3. customThe reagents were removed from the resin
  4. washthe resin was washed with dichloromethane (5 mL), methanol (5 mL), and N,N-dimethylformamide (5 mL)

Sources & evidence

ORD record
ord-5ff1ca3b1ce74c93bc0a7e4b14bfbae4
Source dataset
uspto-grants-2012_07
Patent number
US08227606B2

Reaction notes

Loading…