Morpholine → HCID 86673699, compound

HRID 1046488Notes

Reaction equation

HRID 1046488 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:13]3[C:14]([O:18][CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]=2)[CH:6]=[C:5]1C(O)=O)([CH3:3])[CH3:2].[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.CN([C:56]([O:60]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:13]3[C:14]([O:18][CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:10]=2)[CH:6]=[C:5]1[CH:52]1[N:47]([CH:56]=[O:60])[CH2:48][CH2:49][O:50][CH2:51]1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68069660HCID 68069660, compound

Product 1

HCID 86673699HCID 86673699, compoundYield 97.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-isopropyl-4-(4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)-1H-pyrrole-2-carboxylic acid (150 mg, 0.24 mmol), morpholine (50 mg, 0.98 mmol), HATU (137 mg, 0.36 mmol), DIPEA (0.3 mL) in DMF (10 mL) was stirred overnight at 25° C. Ethyl acetate (100 mL) and water (50 mL) were added. The organic layer was separated and washed by water (30 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the desired product title compound as a yellowish oil (160 mg, 96%) without further purification. LC-MS (Method A): m/z=682.3 [M+H]+; 2.44 min.

Workup

  1. customThe organic layer was separated
  2. washwashed by water (30 mL) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c9d7760c0c14a72bb281b12eb605130
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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