2-Pyridinamine, 5-bromo-6-methyl- → HCID 57718247, compound

HRID 1366837Notes

Reaction equation

HRID 1366837 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([CH3:9])[N:3]=1.[N:10]1([S:16]([C:19]2[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34](Cl)(=[O:36])=[O:35]>>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:25][C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)(=[O:18])=[O:17])=[CH:24][CH:23]=2)=[C:4]([CH3:9])[N:3]=1)(=[O:36])=[O:35]

Participants

4

Reactant 3

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 577182904-(N-piperidinylsulfonyl)thiophenol

Product 1

HCID 57718247HCID 57718247, compound

Procedure

Prepared from 2-amino-5-bromo-6-methylpyridine and 4-(N -piperidinylsulfonyl)thiophenol according to General Method 11 step 1 followed by reaction with 2,4-dichlorophenylsulfonyl chloride according to General Method 11 step 2. 1H NMR (CDCl3): 8.24, 7.76, 7.72, 7.51, 7.19, 7.05 (1 H, 1 H, 2 H, 1 H, 1 H, 2 H, 1 H, 7×d, J 9, 11, 9, 11, 10, 9 Hz, Ar CH's), 7.63 (1 H, s, A-ring CH ortho to 2×Cl), 3.10-3.01 (4H, m, CH2NCH2), 2.58 (3H, s, CH3), 1.76-1.68 (4 H, m, CH2CH2CH2CH2CH2), 1.58-1.47 (2 H, m, CH2CH2CH2CH2CH2). Hplc (Luna 2, Gradient 5): rt=6.40 minutes. LC/MS rt=7.11 minutes, 572/574 (MH+).

Workup

  1. customrt=6.40 minutes
  2. customLC/MS rt=7.11 minutes, 572/574 (MH+)

Sources & evidence

ORD record
ord-fff82032e5794d5bbdfd47f4bf358efe
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

Loading…