(S)-3-[4-(2-amino-6-{1-[2-(6-cyanopyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid → (S)-2-amino-3[4-(2-amino-6-{1-[2-(6-cyano-pyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid

HRID 2233452Notes

Reaction equation

HRID 2233452 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:19]C(OC(C)(C)C)=O)[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)[CH:5]=[C:4]([O:27][CH:28]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]2[CH:40]=[N:41][C:42]([C:45]#[N:46])=[CH:43][CH:44]=2)[C:29]([F:32])([F:31])[F:30])[N:3]=1>FC(F)(F)C(O)=O.ClCCl>[NH2:19][C@@H:15]([CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:5]=[C:4]([O:27][CH:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[CH:40]=[N:41][C:42]([C:45]#[N:46])=[CH:43][CH:44]=3)[C:29]([F:32])([F:30])[F:31])[N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:13][CH:12]=1)[C:16]([OH:18])=[O:17]

Participants

4

Reactant 1

HCID 66743498(S)-3-[4-(2-amino-6-{1-[2-(6-cyanopyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

Product 1

HCID 25024903(S)-2-amino-3[4-(2-amino-6-{1-[2-(6-cyano-pyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acidYield 18.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

80 mg of (S)-3-[4-(2-amino-6-{1-[2-(6-cyanopyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid was dissolved in the solution of 30% trifluoro acetic acid in dichloromethane (5 ml). The mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was purified by preparative HPLC to give 12.6 mg of (S)-2-amino-3[4-(2-amino-6-{1-[2-(6-cyano-pyridin-3-yl)-phenyl]-2,2,2-trifluoro-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid. 1H NMR (400 MHz, CD3OD) δ (ppm) 8.86 (s, 1H), 8.17 (d, J=2 Hz, 1H), 8.15 (d, J=2 Hz, 1H), 7.96 (m, 2H), 7.59 (m, 1H), 7.36 (m, 3H), 6.7 (s, 1H), 6.65 (d, J=6.8 Hz, 1H), 4.25 (m, 1H), 3.47 (m, 1H), 3.23 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cdb33fb3d3744184a1e480658bcd305a
Source dataset
uspto-grants-2010_05
Patent number
US07709493B2

Reaction notes

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