2-Amino-5-bromopyridine → HCID 57718225, compound

HRID 1366840Notes

Reaction equation

HRID 1366840 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N:9]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34]>>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[S:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:24][C:21]2[CH:20]=[CH:19][C:18]([S:15]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)(=[O:17])=[O:16])=[CH:23][CH:22]=2)=[CH:4][N:3]=1)(=[O:35])=[O:34]

Participants

4

Reactant 3

HCID 706222-Amino-5-bromopyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 577182904-(N-piperidinylsulfonyl)thiophenol

Product 1

HCID 57718225HCID 57718225, compound

Procedure

Prepared from 2-amino-5-bromopyridine 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): 11.95 (1 H, br s, NH), 8.55 (1 H, s, Ar CH ortho to 2×Cl), 8.29 (1 H, d, CH ortho to SO2NH), 7.85, 7.61, 7.54 & 7.39 (4×1 H, d, s, d & d, J 11, 10 & 11 Hz, A- & B-ring CH's) 7.73 & 7.30 (2×2 H, 2×d, 2×J 10 Hz, Ar CH's of C-ring), 3.10-3.01 (4H, m, CH2NCH2), 2.18 (3H, s, CH3), 1.79-1.68 (4 H, m, CH2CH2CH2CH2CH2), 1.60-1.48 (2 H, m, CH2CH2CH2CH2CH2). Hplc (Luna 2, Gradient 5): rt=6.48 minutes. LC/MS rt=7.19 minutes, 558/560 (MH+).

Workup

  1. customrt=6.48 minutes
  2. customLC/MS rt=7.19 minutes, 558/560 (MH+)

Sources & evidence

ORD record
ord-bd07228731d54551a3f67a1d464069f6
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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