DL-alanine → HCID 53696734, compound

HRID 1952770Notes

Reaction equation

HRID 1952770 reaction equation
NC(C)C(O)=O.[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:17]=[C:18]([O:58][CH3:59])[C:19]([O:56][CH3:57])=[C:20]([CH:22]=[CH:23][C:24]([N:26]3[N:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]3[C:36]3[CH:55]=[CH:54][C:39]([CH2:40][O:41][C:42](=[O:53])[CH:43]([NH:45]C(OC(C)(C)C)=O)[CH3:44])=[CH:38][CH:37]=3)=[O:25])[CH:21]=2)=[CH:10][N:9]=1.CS(O)(=O)=O>C(O)C(F)(F)F>[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:17]=[C:18]([O:58][CH3:59])[C:19]([O:56][CH3:57])=[C:20]([CH:22]=[CH:23][C:24]([N:26]3[N:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]3[C:36]3[CH:37]=[CH:38][C:39]([CH2:40][O:41][C:42](=[O:53])[CH:43]([NH2:45])[CH3:44])=[CH:54][CH:55]=3)=[O:25])[CH:21]=2)=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 602DL-alanineHCID 6395Methanesulfonic AcidHCID 54473406HCID 54473406, compound

Product 1

HCID 53696734HCID 53696734, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Preparation of 2-amino-propionic acid 4-(2-{3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl -acryloyl}-1,2-dihydro-phthalazin-1-yl)-benzyl ester ##STR16## A solution of 130 mg of 2-tert-butoxycarbonylamino-propionic acid 4-(2-(3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-acryloyl)-1,2-dihydro-phthalazin-1-yl)-benzyl ester in 20 ml of trifluoroethanol is treated with 18 μl of methanesulphonic acid at room temperature over one hour. The reaction solution is concentrated, the residue is taken up in ethyl acetate and filtered. The crystals are dissolved in 5 ml of water and treated with 20 ml of pH 7 buffer. The suspension obtained is suction filtered. There are obtained 65 mg of 2-amino-propionic acid 4-(2-{3-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-acryloyl)-1,2-dihydro-phthalazin-1-yl)-benzyl ester, MS (ISP): 622.3 (M+H)+

Workup

  1. concentrationThe reaction solution is concentrated
  2. filtrationfiltered
  3. dissolutionThe crystals are dissolved in 5 ml of water
  4. additiontreated with 20 ml of pH 7 buffer
  5. customThe suspension obtained

Sources & evidence

ORD record
ord-1a1cf166463f41d0958fe6d6d6f8dfaf
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

Loading…