2-Chloro-6-fluorobenzaldehyde → HCID 54302964, compound

HRID 842644Notes

Reaction equation

HRID 842644 reaction equation
ClC1C=CC=C(F)C=1C=O.ClC1C=CC=C(F)C=1C=C.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C@H:29]1[CH2:31][C@H:30]1[N:32]=[C:33]=[O:34].[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][N:37]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C@H:29]1[CH2:31][C@H:30]1[NH:32][C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][N:37]=1)=[O:34]

Participants

5

Reactant 4

HCID 678472-Chloro-6-fluorobenzaldehydeHCID 8182602-Amino-5-cyanopyridineHCID 121749902-Chloro-6-fluorostyreneHCID 54463356cis-2-(2-Chloro-6-fluorophenyl)cyclopropylisocyanate

Product 1

HCID 54302964HCID 54302964, compound

Procedure

2-chloro-6-fluorobenzaldehyde (Aldrich), was converted to 2-chloro-6-fluorostyrene according to the method described in Example 377 of WO 93/03022 and then to cis-2-(2-chloro-6-fluorophenyl) cyclopropylisocyanate analogously to the method described in Example 348 of WO 93/03022. This compound was then condensed with 2-amino-5-cyanopyridine of Example 41 in a manner analogous to the method in Example 7 to provide N-(cis-2-(2-chloro-6-fluorophenyl)-cyclopropyl)-N′-(5-cyanopyrid-2-yl)-urea: Mp 189° C. 1H -NMR (250 MHz, DMSO-d6): 1.2 (m, 11H), 1.45-1.55 (m, 1H), 2.2-2.3 (m, 1H), 3.3-3.4 (m, 1H), 7.35-7.6 (m, 41z), 7.9-8.1 (m, 2H), 9.5 (s, 1).

Sources & evidence

ORD record
ord-e2c0528020cc4586a57224fa030bc476
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

Loading…