Phosphoric Acid → 3-(6-(3-Acetamido-4-methylphenylamino)-3-cyanoimidazo[1,2-b]pyridazin-8-ylamino)-N-(2-(dimethylamino)ethyl)benzamide

HRID 889474Notes

Reaction equation

HRID 889474 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:13](CC2C=CC(OC)=CC=2)[C:14]2[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=2)[C:17]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[O:18])[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[NH2:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:48])=[C:42]([NH:44][C:45](=[O:47])[CH3:46])[CH:43]=1.OP(O)(O)=O>O.CO>[C:45]([NH:44][C:42]1[CH:43]=[C:38]([NH:37][C:2]2[CH:3]=[C:4]([NH:13][C:14]3[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=3)[C:17]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[O:18])[C:5]3[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=3)[N:7]=2)[CH:39]=[CH:40][C:41]=1[CH3:48])(=[O:47])[CH3:46]

Participants

6

Reactant 3

HCID 1004Phosphoric Acid2×HCID 794922-Acetylamino-4-aminotolueneHCID 593137633-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)-N-(2-(dimethylamino)ethyl)benzamide

Product 1

HCID 593137103-(6-(3-Acetamido-4-methylphenylamino)-3-cyanoimidazo[1,2-b]pyridazin-8-ylamino)-N-(2-(dimethylamino)ethyl)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

Example 253 was prepared from 253D and N-(5-amino-2-methylphenyl)acetamide following the procedure as described in Example 6. HPLC: Rt=3.110 min. (YMC S5 ODS (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.2% H3PO4). Solvent A: (10% MeOH, 90% H2O, 0.2% H3PO4). Gradient, start % B=0, final % B=100, gradient time 4 min., hold at 100% 1 min., flow rate 4 mL/min.). MS (ES): m/z=512.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.04 (1H, br. s.), 9.52-9.58 (2H, m), 9.21 (1H, s), 8.94 (1H, t, J=5.52 Hz), 8.18 (1H, s), 7.87 (1H, s), 7.59-7.63 (2H, m), 7.44-7.54 (2H, m), 7.06 (1H, d, J=8.28 Hz), 6.81-6.85 (1H, m), 3.59 (3H, q, J=5.69 Hz), 3.24 (2H, q, J=5.86 Hz), 2.73-2.84 (6H, m), 2.08 (3H, s), 1.98 (3H, s).

Workup

  1. customB=100, gradient time 4 min.
  2. customhold at 100% 1 min., flow rate 4 mL/min.

Sources & evidence

ORD record
ord-d1fae26cdd984c5d9fb3ecff122b13e5
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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