2-Chloropyrimidine → 4-(4-Amino-3-fluorophenoxy)pyridine-2-carbonitrile hydrochloride

HRID 729903Notes

Reaction equation

HRID 729903 reaction equation
[Cl:1]C1N=CC=CN=1.[NH2:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=2)=[CH:11][C:10]=1[F:24]>>[ClH:1].[NH2:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=2)=[CH:11][C:10]=1[F:24]

Participants

3

Reactant 2

HCID 744042-ChloropyrimidineHCID 551566584-(4-Amino-3-fluorophenoxy)picolinonitrile

Product 1

HCID 671055364-(4-Amino-3-fluorophenoxy)pyridine-2-carbonitrile hydrochloride

Procedure

Starting from chloropyrimide 1A and aniline 2G, this material was prepared by a method analogous to that described for Example 1. After the reaction was complete, the solid was filtered and washed with MeOH to provide the title compound. 1H NMR (DMSO-d6) δ 12.99 (s, broad, 1H, 10.51 (s, broad, 1H) 8.63 (d, J=6.0 Hz, 1H), 8.07 (s, broad, 1H), 7.88 (m, 2H), 7.79 (d, J=2.4 Hz, 1H), 7.66 (m, 3H), 7.45 (dd, J=11.2 Hz, 2.4 Hz, 1H), 7.30 (d, J=3.2 Hz, 1H), 7.16 (dd, J=8.8 Hz, 1.6 Hz, 1H), 6.82 (s, broad, 1H); MS ES: 399 (M+H)+, calcd 399, RT=2.24 min.

Workup

  1. customthis material was prepared by a method analogous to
  2. filtrationthe solid was filtered
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-3835a763f04e49278a5b60e4e4910bc3
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

Loading…