Morpholine → HCID 57741259, compound

HRID 1517666Notes

Reaction equation

HRID 1517666 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[C:13]3[N:14]([C:17]4[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=4)[N:15]=[CH:16][C:12]=3[CH2:11][CH2:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CN(C=O)C>[N:33]1([C:21]([C:20]2[CH:19]=[CH:18][C:17]([N:14]3[C:13]4[C:7]5[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=5[CH2:10][CH2:11][C:12]=4[CH:16]=[N:15]3)=[CH:25][CH:24]=2)=[O:23])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86605022HCID 86605022, compound

Product 1

HCID 57741259HCID 57741259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.5 mg (0.01 mmol) 4-(7-acetylamino-4,5-dihydro-pyrazolo[3′,4′:3,4]benzo[1,2-d]thiazol-1-yl)-benzoic acid (prepared analogously to Example 1) in 0.5 ml DMF is combined with 4 μL (0.03 mmol) triethylamine and 4 mg (0.01 mmol) O-pentafluorophenyl-1,1,3,3-tetramethyluronium hexafluorophosphate (PFTU) and stirred for 15 minutes. A solution of 1 mg (0.01 mmol) morpholine in 0.5 ml DMF is added to this mixture and it is shaken for 12 hours at ambient temperature. Then 3 mg polyamine resin HL (0.01 mmol, 200-400 mesh) are added and the mixture is shaken for a further 8 hours. The resin is filtered off and the filtrate is evaporated to dryness in vacuo.

Workup

  1. stirringis shaken for 12 hours at ambient temperature
  2. stirringthe mixture is shaken for a further 8 hours
  3. filtrationThe resin is filtered off
  4. customthe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8543698807e14b2a9539cf449bdf6487
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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