Hydrochloric Acid → HCID 178479183, compound

HRID 1987060Notes

Reaction equation

HRID 1987060 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([F:32])([F:31])[CH2:9][NH:10][C:11]2[C:12]([F:30])=[C:13]([CH2:19][C:20]([NH:22][CH2:23][CH2:24][O:25][NH:26][C:27](=[NH:29])[NH2:28])=[O:21])[C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.Cl.Cl.CC#N>CC#N>[ClH:1].[C:27]([NH:26][O:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[CH2:19][C:13]1[C:14]([C:17]#[N:18])=[CH:15][CH:16]=[C:11]([NH:10][CH2:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)([F:31])[F:32])[C:12]=1[F:30])(=[NH:28])[NH2:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22261314Acetonitrile--hydrogen chloride (1/1)HCID 178510051HCID 178510051, compound

Product 1

HCID 178479183HCID 178479183, compoundYield 176.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a homogeneous pale yellow solution of 2-{3-[2-(3-chlorophenyl)-2,2-difluoroethylamino]-6-cyano-2-fluorophenyl}-N-(2-amidinoaminooxyethyl)acetamide (1.28 g, 2.74 mmol), as prepared in the preceding step, in dry MeCN (38 mL) was added anhydrous HCl (0.283 M in MeCN, 10.2 mL, 2.89 mmol) rapidly at room temperature in five ˜2 mL portions with swirling. Immediately following addition of the last portion of HCl/MeCN, the solution was allowed to sit undisturbed at room temperature for 15 min, and the resulting crystals were filtered and dried under vacuum to afford the title compound (1.22 g, 88%) as off-white microcrystals. 1H NMR (300 MHz, CD3OD) δ 7.57-7.54 (m, 1H), 7.52-7.41 (m, 3H), 7.29 (dd, J=8.6 Hz, 1.3 Hz, 1H), 6.80 (t, J=8.6 Hz, 1H), 3.95 (t, J=5.4 Hz, 2H), 3.94 (t, J=13.7 Hz, 2H), 3.76 (d, J=2.0 Hz, 2H), 3.52 (t, J=5.4 Hz, 2H). LC/MS (ESI) calcd for C20H21ClF3N6O2 (MH+) 469.1. found 469.1. Elem. Anal. Calc. for free base •1.00 HCl: C, 47.54; H, 4.19; N, 16.63; Cl, 7.02. Found: C, 47.42; H, 4.03; N, 16.62; Cl, 7.02. Karl Fischer % water: <0.10.

Workup

  1. filtrationthe resulting crystals were filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-179c795aa5f04f11bc03877dea35bdfb
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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