Ammonia → HCID 11394995, compound

HRID 993326Notes

Reaction equation

BrCC(=O)CC.FC1C=C[C:11]([C:14]2[N:15]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:19]([C:29]4[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=4)=[C:16]3[O:17][CH:18]=2)=[CH:10]C=1.N>>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[C:19]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=3)=[C:16]3[O:17][CH:18]=[C:14]([CH2:11][CH3:10])[N:15]3[N:21]=2)=[CH:27][CH:26]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 131561-Bromo-2-butanone

HCID 11362918HCID 11362918, compound

Product 1

HCID 11394995HCID 11394995, compound

Procedure

The desired product was prepared according to the method of Example 73D-73E substituting 1-bromo-2-butanone in place of 4′-fluoro-2-bromoacetophenone. The resulting thio-ether product was then oxidized as described in Example 73F (yield: 68 mg, 10%). MP 205-208° C.; MS (DCI-NH3) m/z 357(M+H)+, m/z 374 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ1.35 (t, J=7 Hz, 3H), 2.85 (q, J=7 Hz, 2H), 3.25 (s, 3H) 7.3 (m, 2H), 7.5 (m, 4H), 7.8 (d, J=9 Hz, 2H), 8.04 (s, 1H); Anal. calc. for C20H17FN2O3S: C, 62.49; H, 4.46; N, 7.29. Found C, 62.28; H, 4.36; N, 6.95.

Sources & evidence

ORD record: ord-cf896b0ea6d54a339868138df71336d9
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472416B1

Reaction notes

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