Succinic anhydride → Succinic acid mono-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl}-ester

HRID 28576Notes

Reaction equation

HRID 28576 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[N:3]=1.[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28]1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:27](=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 10406874Benzenemethanol, 4-((2-amino-6-(5-chloro-2-ethoxyphenyl)-4-pyrimidinyl)amino)-

Product 1

HCID 11431366Succinic acid mono-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl}-esterYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of the title compound of Example 44 (0.300 g, 0.809 mmol) and succinic anhydride (0.097 g, 0.971 mmol) in chloroform (10 ml) was added 4-dimethyl-amino-pyridine (0.138 g, 1.13 mmol). After stirring for 16 hours, the mixture was concentrated under reduced pressure. Water (10 ml) was added and the mixture was adjusted to pH 2 by addition of aqueous potassium hydrogen sulfate solution (0.5 M). The solid was filtered and dried under reduced pressure to provide the title compound (0.381 g, 81% yield). 1H NMR (DMSO-d6) δ1.38 (t, 3H, J=6.9 Hz, CH3), 2.48-2.50 (m, 2H, CH2), 2.50-2.52 (m, 2H, CH2), 4.13 (q, 2H, J=6.9 Hz, CH2), 5.05 (s, 2H, CH2), 6.28 (s, 2H, NH2), 6.79 (s, 1H, Ar), 7.14 (d, 1H, J=8.9 Hz, Ar), 7.29 (d, 2H, J=8.9 Hz, Ar), 7.41 (dd, 1H, J=8.9 Hz, 2.9 Hz, Ar), 7.71 (d, 2H, J=8.5 Hz, Ar), 7.93 (s, 1H, Ar), 9.22 (s, 1H, NH), 12.05 (s, 1H, COOH).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater (10 ml) was added
  3. additionthe mixture was adjusted to pH 2 by addition of aqueous potassium hydrogen sulfate solution (0.5 M)
  4. filtrationThe solid was filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a5cb20e1306e4cf3a1c8fe7d5cdf7764
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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