Ethyl isocyanate → HCID 59321022, compound

HRID 341240Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[CH:13]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>COCCOC>[CH2:31]([NH:33][C:34]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]2[CH:15]=[N:14][N:12]3[CH:13]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH:9]=[CH:10][C:11]=23)[CH:18]=1)=[O:35])[CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3-[6-(4-fluoro-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]-phenylamine (Example 118, 50 mg, 0.16 mmol), Et3N (45 μL, 0.32 mmol) and ethyl isocyanate (26 μL, 0.32 mmol) in dry DME (2 ml) was stirred and heated at 60° C. under N2 for 24 hours [Further ethyl isocyanate (30 μL) was added after 7 hours]. The reaction mixture was evaporated and dried under vacuum to give the title compound (55 mg, solid). 1H NMR (400 MHz, DMSO-d6): 9.09 (1H, s), 8.53 (1H, s), 8.36 (1H, s), 8.02 (1H, d), 7.93-7.83 (3H, m), 7.72 (1H, dd), 7.38-7.29 (3H, m), 7.27-7.22 (2H, m), 6.15 (1H, t), 3.19-3.09 (2H, m), 1.08 (3H, t).

Workup

customThe reaction mixture was evaporated
customdried under vacuum

Sources & evidence

ORD record: ord-7c8889e9859e4261b76fe887129e544e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895745B2

Reaction notes

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