4-Methylmorpholine → HCID 178427372, compound

HRID 1665126Notes

Reaction equation

HRID 1665126 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N=C=N.Cl.Cl.[NH:24]1[C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][NH:26]/[C:25]/1=[N:34]\[C:35]([C:37]1[C:42]([NH2:43])=[N:41][C:40]([NH2:44])=[C:39]([Cl:45])[N:38]=1)=[O:36].CN1CCOCC1>CN1C(=O)CCC1>[C:1]1([CH3:18])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([N:31]3[CH2:32][CH2:33][C:28]4([NH:24]/[C:25](=[N:34]/[C:35]([C:37]5[C:42]([NH2:43])=[N:41][C:40]([NH2:44])=[C:39]([Cl:45])[N:38]=5)=[O:36])/[NH:26][CH2:27]4)[CH2:29][CH2:30]3)=[O:17])=[CH:11]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 160435CarbodiimideHCID 27246931-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acidHCID 178478673HCID 178478673, compound

Product 1

HCID 178427372HCID 178427372, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 1-(Toluene-4-sulfonyl)-1H-pyrrole-3-carboxylic acid (0.023 g, 0.085 mmol) in NMP (850 □l) is added to PS-carbodiimide (190 mg of 1.3 mmol/g loading, 0.24 mmol), followed by a solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide dihydrochloride (Ex. 38) (0.08 mmol) and N-methyl morpholine (8 □l, 0.08 mmol) in NMP (1 ml), and the resulting reaction mixture is shaken at room temperature. The reaction mixture is filtered and the resin is washed with NMP (1 ml). The collected filtrate is concentrated in vacuo and the residues are purified by mass-directed preparative HPLC. The purified fractions are evaporated under vacuum to afford the title compound; [M+H]+ 572.08

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture is filtered
  3. washthe resin is washed with NMP (1 ml)
  4. concentrationThe collected filtrate is concentrated in vacuo
  5. customthe residues are purified by mass-directed preparative HPLC
  6. customThe purified fractions are evaporated under vacuum

Sources & evidence

ORD record
ord-f1de0c0c2c7444218adc86902f7ecc23
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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