Hydrochloric Acid → HCID 178490278, compound

HRID 216127Notes

Reaction equation

HRID 216127 reaction equation
COC1N=C(C2C=C(CC#N)C=CC=2)C=C(NCCC2C=CC(OC)=CC=2)N=1.COC1N=C(C2C=C(C=CC=2)C#N)C=C(NCCC2C=CC(OC)=CC=2)N=1.[CH3:56][O:57][C:58]1[CH:63]=[CH:62][C:61]([CH2:64][CH2:65][NH:66][C:67]2[CH:72]=[C:71]([C:73]3[CH:78]=[CH:77][CH:76]=[C:75]([CH2:79][C:80]4[NH:84][N:83]=[N:82][N:81]=4)[CH:74]=3)[N:70]=[C:69]([O:85][CH3:86])[N:68]=2)=[CH:60][CH:59]=1.[ClH:87]>CCOC(C)=O>[ClH:87].[CH3:56][O:57][C:58]1[CH:63]=[CH:62][C:61]([CH2:64][CH2:65][NH:66][C:67]2[CH:72]=[C:71]([C:73]3[CH:78]=[CH:77][CH:76]=[C:75]([CH2:79][C:80]4[NH:84][N:83]=[N:82][N:81]=4)[CH:74]=3)[N:70]=[C:69]([O:85][CH3:86])[N:68]=2)=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11660493HCID 11660493, compoundHCID 53321838HCID 53321838, compoundHCID 178490277HCID 178490277, compound

Product 1

HCID 178490278HCID 178490278, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By proceeding in a similar manner to Example 24(a) above but substituting, (3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-acetonitrile [Example 35(s)] for 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzonitrile, there is prepared [2-(4-methoxy-phenyl)-ethyl]-{2-methoxy-6-[3-(1H-tetrazol-5-ylmethyl)-phenyl]-pyrimidin-4-yl}-amine. This material is treated with a solution of hydrochloric acid in EtOAc followed by lyophilization to afford [2-(4-methoxy-phenyl)-ethyl]-{2-methoxy-6-[3-(1H-tetrazol-5-ylmethyl)-phenyl]-pyrimidin-4-yl}-amine hydrochloride (134 mg, Example 24(b)]. LCMS: RT=2.62 minutes, MS: 418 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □9.65 (1H, brs), 7.7-7.5 (4H, m), 7.2 (2H, d, J=8.4 Hz), 6.87 (2H, d, J=8.4 Hz), 6.68 (1H, s), 4.4 (2H, s), 4.08 (3H, s), 3.71 (3H, s), 3.6 (2H, m), 2.85 (2H, t, J=7.2 Hz). IC50=0.1 nM

Sources & evidence

ORD record
ord-93e8b371753649a3be7e41995115ecfa
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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