4-Methylmorpholine → HCID 178462099, compound

HRID 2053956Notes

Reaction equation

HRID 2053956 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:14]2[CH2:15][CH2:16][CH2:17][C:13]=2[N:12]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][C:19]=2[C:27]([F:30])([F:29])[F:28])[N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:32](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[Cl:60][C:61]1[CH:72]=[CH:71][C:64]2[NH:65][C:66]([CH2:68][CH2:69]N)=[N:67][C:63]=2[CH:62]=1.ClCCl.CO.N.ClCl>CN1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:14]2[CH2:15][CH2:16][CH2:17][C:13]=2[N:12]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH:32][C@H:68]([C:66]3[NH:65][C:64]4[CH:71]=[CH:72][C:61]([Cl:60])=[CH:62][C:63]=4[N:67]=3)[CH3:69])=[O:24])=[CH:20][C:19]=2[C:27]([F:30])([F:29])[F:28])[N:11]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 24526Chlorine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21584172Ammonia methanol dichloromethaneHCID 69312589HCID 69312589, compoundHCID 178510880HCID 178510880, compound

Product 1

HCID 178462099HCID 178462099, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

Prepared analogously to Example 1g from 4-[3-(tert-butoxycarbonylamino)methyl-5,6-dihydro-4H-cyclopentapyrazol-1-yl]-3-trifluoromethylbenzoic acid, TBTU, N-methylmorpholine, and 5-chloro-1H-benzimidazol-2-ylethylamine in N-methylpyrrolidine. Yield: 30%; Rf value: 0.65 (silica gel; dichloromethane/methanol/ammonia=9:1:0.1); C29H30ClF3N6O3 (603.04); mass spectrum: (M+H)+=603/605 (chlorine isotope) and (M−H)-=601/603 (chlorine isotope).

Sources & evidence

ORD record
ord-1aae0808a3594f32ae4b142e3cb2195e
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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