Hydrochloric Acid → HCID 86614446, compound

HRID 1038099Notes

Reaction equation

HRID 1038099 reaction equation
CCN=C=NCCCN(C)C.Cl.Cl.C1C=CC2N(O)N=NC=2C=1.O.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([NH2:41])[CH:39]=3)[N:34]([C:42]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:33]=2)=[CH:28][CH:27]=1.[CH:61]([N:63]([CH3:93])[C:64]1([C:90](O)=[O:91])[CH2:68][CH2:67][N:66]([CH2:69][C:70](=[O:89])[N:71]2[CH2:76][CH:75]=[C:74]([C:77]3[CH:82]=[CH:81][C:80]([C:83]4[N:88]=[CH:87][CH:86]=[CH:85][N:84]=4)=[CH:79][CH:78]=3)[CH2:73][CH2:72]2)[CH2:65]1)=[O:62].[Li]>CN(C=O)C.CN1CCOCC1>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([NH:41][C:90]([C:64]4([N:63]([CH:61]=[O:62])[CH3:93])[CH2:68][CH2:67][N:66]([CH2:69][C:70](=[O:89])[N:71]5[CH2:72][CH:73]=[C:74]([C:77]6[CH:78]=[CH:79][C:80]([C:83]7[N:88]=[CH:87][CH:86]=[CH:85][N:84]=7)=[CH:81][CH:82]=6)[CH2:75][CH2:76]5)[CH2:65]4)=[O:91])[CH:39]=3)[N:34]([C:42]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:33]=2)=[CH:30][CH:31]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 57685763HCID 57685763, compoundHCID 67420013HCID 67420013, compound

Product 1

HCID 86614446HCID 86614446, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 79724-MethylmorpholineSolvent

Procedure

Added EDCl.HCl (75 mg, 0.39 mmol) and HOBT.H2O (50 mg, 0.37 mmol) to a solution of 3-(4-Fluoro-phenyl)-1trityl-indazol-5-ylamine (110 mg, 0.234 mmol) and 3-(Formyl-methyl-amino)-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid, Lithium salt (6T) (95 mg, 0.211 mmol) in DMF (2 ml) and NMM (0.1 ml) at room temperature, then stirred overnight. The solvent was evaporated and residue extracted with MeCl2 (50 ml), washed with H2O (20 ml), dried over MgSO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with v/v 9:1 EtOAc:Hexanes yielding 7T as a white solid (89 mg, 44%) ESMS (MH 901).

Workup

  1. customThe solvent was evaporated
  2. extractionresidue extracted with MeCl2 (50 ml)
  3. washwashed with H2O (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding a residue which
  8. customchromatographed on silica gel eluting with v/v 9:1 EtOAc

Sources & evidence

ORD record
ord-fdcf9a1da70243a3ba5d01ca7752d09d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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