4-Methylmorpholine → HCID 86651889, compound

HRID 1183023Notes

Reaction equation

HRID 1183023 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[C:50]([O:54][C:55](=[O:76])[NH:56][C@H:57]([CH2:63][NH:64][C:65]([C:67]1[C:72]([NH2:73])=[N:71][C:70]([NH2:74])=[C:69]([Cl:75])[N:68]=1)=[O:66])[CH2:58][CH2:59][CH2:60][CH2:61][NH2:62])([CH3:53])([CH3:52])[CH3:51]>CN(C=O)C>[C:50]([O:54][C:55](=[O:76])[NH:56][C@H:57]([CH2:63][NH:64][C:65]([C:67]1[C:72]([NH2:73])=[N:71][C:70]([NH2:74])=[C:69]([Cl:75])[N:68]=1)=[O:66])[CH2:58][CH2:59][CH2:60][CH2:61][NH:62][C:16](=[O:18])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)([CH3:53])([CH3:51])[CH3:52]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 810334-Benzyloxyphenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86651890HCID 86651890, compound2×

Product 1

HCID 86651889HCID 86651889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-benzyloxy-phenyl-acetic acid (39 mg, 0.16 mmol) and HATU (61 mg, 0.16 mmol) in DMF (3 mL) is added N-methylmorpholine (64 mg, 0.64 mmol) followed by a solution of ((S)-5-amino-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (Intermediate C) (64 mg, 0.16 mmol) in DMF (2 mL). The resulting mixture is stirred at RT for 17 h. The solvent is removed in vacuo to afford the title compound which is used in the next step without further purification. [M+H]+ 626.

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9e8ee31375ef433fbe66060c83a33011
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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