Hydrochloric Acid → HCID 10279265, compound

HRID 397532Notes

Reaction equation

HRID 397532 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10]C(=O)OC(C)(C)C)=[C:4]([CH2:18][NH:19][C:20](=[O:41])[CH2:21][C:22]2[C:27]([Cl:28])=[CH:26][N:25]=[C:24]([NH:29][CH2:30][C:31]([F:39])([F:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[C:23]=2[F:40])[CH:3]=1.Cl>CCOC(C)=O>[NH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:18][NH:19][C:20](=[O:41])[CH2:21][C:22]1[C:27]([Cl:28])=[CH:26][N:25]=[C:24]([NH:29][CH2:30][C:31]([F:38])([F:39])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[C:23]=1[F:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10282444HCID 10282444, compound

Product 1

HCID 10279265HCID 10279265, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 0.04 g (0.065 mmol) tert-butyl 2-[4-chloro-2-({[(5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetyl]amino}methyl)phenyl]ethylcarbamate 1-10 in 2 mL EtOAc/1 mL MeOH was passed through a steady stream of HCl gas for 5 minutes, then the reaction mixture was concentrated to give N-[2-(2-aminoethyl)-5-chlorobenzyl]-2-(5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetamide 1-11. 1H NMR (400 mHz, CD3OD) δ8.71 (d, 1H, J=4.58 Hz); 8.15 (apparent t, 1H, J=7.51 Hz); 7.89 (d, J=8.06 Hz); 7.70 (m, 2H); 7.29(d, 1H, J=1.84 Hz); 7.28 (dd, 1H, J=2.01 and 8.24 Hz); 7.23 (d, 1H, J=8,24 Hz); 4.42 (s, 2H); 4.36 (t, 2H, J=13.5 Hz); 3.80 (s, 2H); 3.41 (m, 2H); 3.02 (m, 2H). Mass Spectrum (electrospray) M+H=512.2

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d90f8b8974b34c2a8260a74a8ebe1917
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

Loading…