4-Methylmorpholine → HCID 178450256, compound

HRID 2281586Notes

Reaction equation

HRID 2281586 reaction equation
[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([OH:20])=O)(=[O:14])=[O:13])[CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH:50]1[C:54]2([CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:53][NH:52]/[C:51]/1=[N:60]\[C:61]([C:63]1[C:68]([NH2:69])=[N:67][C:66]([NH2:70])=[C:65]([Cl:71])[N:64]=1)=[O:62].CN1CCOCC1>CN(C=O)C>[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([N:57]2[CH2:58][CH2:59][C:54]3([NH:50]/[C:51](=[N:60]/[C:61]([C:63]4[C:68]([NH2:69])=[N:67][C:66]([NH2:70])=[C:65]([Cl:71])[N:64]=4)=[O:62])/[NH:52][CH2:53]3)[CH2:55][CH2:56]2)=[O:20])(=[O:14])=[O:13])[CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670866863-(4-Isobutoxy-piperidine-1-sulfonyl)-benzoic acidHCID 178478673HCID 178478673, compound

Product 1

HCID 178450256HCID 178450256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(4-Isobutoxy-piperidine-1-sulfonyl)-benzoic acid (0.03 mmol, 10.2 mg) is treated with a solution of HATU (11.4 mg, 0.03 mmol) in DMF (1 ml) 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) (11.9 mg, 0.03 mmol) and N-methyl morpholine (0.010 ml, 0.03 mmol) in DMF (1 ml) and shaken at room temperature overnight. The solution is evaporated under vacuum, redissolved in DMSO (0.5 ml) and purified by mass-directed preparative HPLC. The purified fractions are evaporated under vacuum to afford the title compound; [M+H]+ 648.4

Workup

  1. customThe solution is evaporated under vacuum
  2. dissolutionredissolved in DMSO (0.5 ml)
  3. custompurified by mass-directed preparative HPLC
  4. customThe purified fractions are evaporated under vacuum

Sources & evidence

ORD record
ord-6004b7b960e448d99c0dcb0e0b660e29
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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