4-Methylmorpholine → HCID 178522649, compound

HRID 270971Notes

Reaction equation

HRID 270971 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]3[N:18]([N:28]=[C:29]([C:31]([OH:33])=O)[CH:30]=3)[C:19](=[O:27])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[NH2:41][C:42]1[NH:46][N:45]=[N:44][N:43]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C=O>[NH:43]1[C:42]([NH:41][C:31]([C:29]2[CH:30]=[C:17]3[NH:16][C:15]([C:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[CH:10][CH:11]=4)=[C:20]([CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[C:19](=[O:27])[N:18]3[N:28]=2)=[O:33])=[N:46][N:45]=[N:44]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 178509299HCID 178509299, compoundHCID 178524067HCID 178524067, compound

Product 1

HCID 178522649HCID 178522649, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 71 mg (0.16 mmol) of 5-(4-benzyloxy-phenyl)-6-cyclohexyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid in 4 mL of dimethylformamide (DMF) was added 0.053 mL (0.48 mmol) of 4-methyl-morpholine, 14 mg (0.164 mmol) of 5-aminotetrazole, followed by 100 mg (0.192 mmol) of PYBOP when the solution turned yellow, and the resulting mixture was stirred at rt for 41 h. The reaction mixture was concentrated to give a residue which was purified via reverse-phase chromatography to afford 29 mg (35% yield) of desired 5-(4-benzyloxy-phenyl)-6-cyclohexyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (1H-tetrazol-5-yl)-amide (540) as a solid as indicated by 1H-NMR; LC-MS calcd. for C27H26N8O3 [M++H]+: 511.21; found: 511.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a residue which
  3. customwas purified via reverse-phase chromatography

Sources & evidence

ORD record
ord-53fc45b845ae45698521c4b7fe71b71e
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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