Hydrochloric Acid → Amino acetic acid-4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester

HRID 28578Notes

Reaction equation

HRID 28578 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15](=[O:25])[CH2:16][NH:17]C(OC(C)(C)C)=O)=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH2:36][CH3:37])[N:3]=1.Cl>C(OCC)(=O)C.O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15](=[O:25])[CH2:16][NH2:17])=[CH:26][CH:27]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH2:36][CH3:37])[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68983979Tert-butoxycarbonylamino-acetic acid 4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester

Product 1

HCID 11235689Amino acetic acid-4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butoxycarbonylamino-acetic acid 4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester in ethyl acetate (15 ml) was treated with a solution of hydrogen chloride in dioxane (4.0 M, 15 ml). After stirring for 16 hours, the solid was filtered and dried under reduced pressure to provide the hydrochloride salt of the title compound (0.273 g, 48% yield). 1H NMR (DMSO-d6) δ 1.39 (t, 3H, J=6.4 Hz, CH3), 3.89 (d, 2H, J=4.9 Hz, CH2), 4.17 (q, 2H, J=6.2 Hz, CH2), 5.25 (s, 2H, CH2), 6.70 (s, 1H, Ar), 7.28 (d, 1H, J=8.7 Hz, Ar), 7.46 (d, 2H, J=8.4 Hz, Ar), 7.62-7.67 (m, 2H, Ar), 7.88 (d, 2H, J=7.4 Hz, Ar), 8.37 (s, 3H), 11.10 (s, 1H), 12.68 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-f99af370631c41c190313fe2b2841e29
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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