2-(Trifluoromethoxy)benzoyl Chloride → HCID 69072454, compound

HRID 1822024Notes

Reaction equation

HRID 1822024 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([Cl:8])=[O:7].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[O:23][CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1>>[ClH:8].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3][C:2]([F:14])([F:13])[F:1])=[CH:18][C:17]=1[O:23][CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 27772412-(Trifluoromethoxy)benzoyl ChlorideHCID 54269594HCID 54269594, compound

Product 1

HCID 69072454HCID 69072454, compound

Procedure

Using a method similar to Example 5, using 2-trifluoromethoxy-benzoyl chloride (0.066 ml, 0.439 mmol) and 4-chloro-3-(1-methyl-piperidin-4-yloxy)-phenylamine (preparation 31) gives the title compound as the free base (132 mg, 77%). Following a method similar to Example 2 gives the title compound as the hydrochloride salt (141 mg, pale yellow solid). Mp: 95-7° C.; mass spectrum (free base, ion spray): m/z=429.2 (M+1), 1H NMR (free base, CDCl3): 8.43 (bs, N—H), 7.98 (dd, J=1.7 Hz, 7.9 Hz, 1H), 7.65 (d, J=2.4 Hz, 1H), 7.53 (td, J=1.7 Hz, 7.9 Hz, 1H), 7.41 (t, J=7.6 Hz, 1H), 7.33-7.25 (m, 2H), 6.87 (dd, J=2.4 Hz, 8.6 Hz, 1H), 4.46-4.38 (bm, 1H), 2.69-2.61 (bm, 2H), 2.37-2.29 (bm, 2H), 2.28 (s, 3H), 2.03-1.86 (bm, 4H). Analysis calculated for C20H21Cl2F3N2O3: C, 51.63; H, 4.55; N, 6.02. Found C, 51.33; H, 4.58; N, 5.88.

Sources & evidence

ORD record
ord-08a6dbb2de144ca6afd20345ae2a415d
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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