Acetic Acid → HCID 10140109, compound

HRID 1435754Notes

Reaction equation

HRID 1435754 reaction equation
C([O:5][C:6](=[O:44])[CH:7]([NH:36]C(OC(C)(C)C)=O)[CH2:8][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[N:26]=[C:25]([NH2:27])[N:24]=[C:23]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[CH3:35])[N:22]=2)=[CH:16][CH:15]=1)=[O:11])(C)(C)C.C(O)(=O)C.ClCCl.Cl>O1CCOCC1.C(OCC)(=O)C>[NH2:27][C:25]1[N:24]=[C:23]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[CH3:35])[N:22]=[C:21]([NH:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C@H:7]([NH2:36])[C:6]([OH:44])=[O:5])=[CH:19][CH:18]=2)[N:26]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 69018876HCID 69018876, compound

Product 1

HCID 10140109HCID 10140109, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-tert-butoxycarbonylamino-pentanedioic acid 5-{4-[4-amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-ylamino]-benzyl}ester 1-tert-butyl ester (1.45 g, 2.3 mmol), acetic acid (10 ml), dichloromethane (5 ml), and a solution of hydrogen chloride in 1,4-dioxane (4 M, 10 ml) was stirred for 12 hours. The mixture was poured into ethyl acetate (50 ml). The solid was filtered and dried under reduced pressure to provide the hydrochloride salt of the title compound (0.98 g, 75% yield). 1H NMR (CD3OD) δ 7.78 (s, 1H), 7.7-7.9 (br s, 2H), 7.58 (d, 2H), 7.46 (d, 4H), 5.18 (s, 2H) 4.09 (t, 1H) 2.58-2.82 (m, 2H) 2.58 (br s, 3H), 2.1-2.3 (m, 2H).

Workup

  1. filtrationThe solid was filtered
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-7894c315a44741219364628341a95cbb
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

Loading…