HCID 59513668, compound → HCID 59513851, compound

HRID 1159991Notes

Reaction equation

HRID 1159991 reaction equation
Cl[C:2]1N=C(C2C(C3C=C(NC(=O)C4C=C(F)C=CC=4F)C=CC=3)=NN3C=CC=CC=23)C=CN=1.[NH2:34][CH2:35][C:36]1[CH:37]=[C:38]([NH:42][C:43]2[N:48]=[C:47]([C:49]3[C:50]([C:58]4[CH:59]=[C:60]([NH:64][C:65](=[O:74])[C:66]5[C:71]([F:72])=[CH:70][CH:69]=[CH:68][C:67]=5[F:73])[CH:61]=[CH:62][CH:63]=4)=[N:51][N:52]4[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=34)[CH:46]=[CH:45][N:44]=2)[CH:39]=[CH:40][CH:41]=1>CC(O)C.Cl.CCOC(C)=O>[F:73][C:67]1[CH:68]=[CH:69][CH:70]=[C:71]([F:72])[C:66]=1[C:65]([NH:64][C:60]1[CH:61]=[CH:62][CH:63]=[C:58]([C:50]2[C:49]([C:47]3[CH:46]=[CH:45][N:44]=[C:43]([NH:42][C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([CH2:35][NH:34][CH3:2])[CH:37]=4)[N:48]=3)=[C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][N:52]3[N:51]=2)[CH:59]=1)=[O:74]

Participants

6

Reactant 2

HCID 59513668HCID 59513668, compoundHCID 59513882HCID 59513882, compound

Product 1

HCID 59513851HCID 59513851, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a suspension of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,5-difluorobenzamide (100 mg, 0.22 mmol) (prepared according to a procedure similar to that described in Example 43, Step A) and N-[(3-aminophenyl)methyl]-2,2,2-trifluoroacetamide (59 mg, 0.27 mmol) (prepared as described in Example 180) in 2-propanol (3 mL) was added 2 drops of concentrated HCl. The mixture was heated to 180° C. in a microwave for 15 min. The reaction mixture was diluted with 25 mL EtOAc and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and purified by flash chromatography to give the title compound (90 mg, 64% yield). 1H NMR (400 MHz, d6-DMSO): δ 10.64 (s, 1H), 9.99 (t, J=5.7 Hz, 1H), 9.63 (s, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.53 (d, J=8.8 Hz, 1H), 8.27 (d, J=5.3 Hz, 1H), 8.04 (s, 1H), 7.86 (d, J=8.1 Hz, 1H), 7.71 (s, 1H), 7.67 (d, J=8.3 Hz, 1H), 7.42-7.55 (m, 5H), 7.35 (d, J=7.5 Hz, 1H), 7.24 (t, J=7.9 Hz, 1H), 7.14 (t, J=6.8 Hz, 4H), 6.85 (d, J=7.3 Hz, 1H), 6.54 (d, J=5.1 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H). MS (ESI) m/z=645 [M+H]+.

Workup

  1. customprepared
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-808e5262c8f34b23983799ae7d6319eb
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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