Acetic Acid → HCID 10140109, compound

HRID 1591623Notes

Reaction equation

HRID 1591623 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-bba8d3c763ba4f52a78557663504bac0
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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