2-Chloro-6-fluorobenzothiazole → HCID 86656486, compound

HRID 75768Notes

Reaction equation

HRID 75768 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].Cl[C:19]1[S:20][C:21]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=2[N:23]=1>>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:19]3[S:20][C:21]4[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 20498702-Chloro-6-fluorobenzothiazoleHCID 673534853-(3-Amino-phenyl)-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 86656486HCID 86656486, compound

Procedure

The title compound was prepared by reacting 3-(3-amino-phenyl)-isoxazole-5-carboxylic acid ethyl ester with 2-chloro-6-fluoro-benzothiazole as described in Example 1, step 3. The solid was separated, filtered, washed with EtOH and dried to give the title compound in 90% yield. Mass (ES+), 384 (M++1); IR (KBr): 3423 (br), 2666 (br), 1723, 1629, 1598; 1H NMR (DMSO-d6) δ: 1.33 (t, 3H), 4.39 (q, 2H), 7.15 (m, 1H), 7.52 (m, 1H), 7.61 (m, 2H), 7.82 (s, 1H), 7.74 (m, 1H), 7.97 (m, 1H), 8.34 (m, 1H), 10.97 (br, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe solid was separated
  3. filtrationfiltered
  4. washwashed with EtOH
  5. customdried

Sources & evidence

ORD record
ord-199e6b45ecc84b7a80d1d68c4cc56b6c
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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