Diisopropylethylamine → HCID 178502366, compound

HRID 1800802Notes

Reaction equation

HRID 1800802 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[C:16]2([CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:15][CH2:14][CH:13]1C(O)=O)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].CC(C)[C@H](NC(OC)=O)C(N1C([C:45]([NH:47][CH2:48][C:49]([C:51]2[CH:56]=[CH:55][C:54]([C:57]3[CH:62]=[CH:61][C:60]([C:63]4[N:64]=[C:65]([C@@H:68]5[CH2:72][CH2:71][CH2:70][N:69]5[C:73](=[O:83])[C@@H:74]([NH:78][C:79]([O:81][CH3:82])=[O:80])[CH:75]([CH3:77])[CH3:76])[NH:66][CH:67]=4)=[CH:59][CH:58]=3)=[CH:53][CH:52]=2)=[O:50])=[O:46])CC2(CN(C(OC(C)(C)C)=O)C2)C1)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl>[CH3:76][CH:75]([CH3:77])[C@H:74]([NH:78][C:79](=[O:80])[O:81][CH3:82])[C:73]([N:69]1[CH2:70][CH2:71][CH2:72][C@H:68]1[C:65]1[NH:66][CH:67]=[C:63]([C:60]2[CH:59]=[CH:58][C:57]([C:54]3[CH:55]=[CH:56][C:51]([C:49](=[O:50])[CH2:48][NH:47][C:45]([CH:13]4[CH2:14][CH2:15][C:16]5([CH2:21][CH2:20][O:19][CH2:18][CH2:17]5)[N:12]4[C:10](=[O:11])[C@@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:7]([CH3:9])[CH3:8])=[O:46])=[CH:52][CH:53]=3)=[CH:62][CH:61]=2)[N:64]=1)=[O:83]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 583130871-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylic acidHCID 178502284HCID 178502284, compound

Product 1

HCID 178502366HCID 178502366, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylic acid (168) (52 mg, 1.5 mmol) and methyl {(1S)-1-[((2S)-2-{4-[4′-(aminoacetyl)-4-biphenylyl]-1H-imidazol-2-yl}-pyrrolidinyl)carbonyl]-2-methylpropyl}carbamate dihydrochloride (1) (88 mg, 0.15 mmol) and HATU (58 mg, 0.15 mmol) in anhydrous dichloromethane (1.2 mL) was added Hunig's base (0.12 mL, 0.68 mmol) and the reaction stirred at room temperature for 1 h. The reaction was concentrated in vacuo and purified by HPLC eluting with 10-90% water/acetonitrile/0.2% NH4OH to afford the title compound as an off-white solid (73 mg, 58% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by HPLC
  3. washeluting with 10-90% water/acetonitrile/0.2% NH4OH

Sources & evidence

ORD record
ord-884f824a59ee429bad0aaf74eec09105
Source dataset
uspto-grants-2013_01
Patent number
US08344155B2

Reaction notes

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