Hydrochloric Acid → 6-{2-(2-Chloro-phenyl)-5-[4-(Pyrimidin-2-yloxy)-phenyl]-pyrrol-1-ylmethyl}-pyridin-2-ylamine hydrochloride

HRID 15010Notes

Reaction equation

HRID 15010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[CH:11][CH:12]=1.Cl>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11525293HCID 11525293, compound

Product 1

HCID 468931726-{2-(2-Chloro-phenyl)-5-[4-(Pyrimidin-2-yloxy)-phenyl]-pyrrol-1-ylmethyl}-pyridin-2-ylamine hydrochlorideYield 186.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 6-{2-(2-chlorophenyl)-5-[4-(pyrimidin-2-yloxy)-phenyl]pyrrol-1-ylmethyl}pyridin-2-ylamine (0.032 g, 0.070 mmol) in diethyl ether (1 mL) was added a 2.0 M solution of HCl (0.035 mL, 0.070 mmol) in diethyl ether and the mixture stirred at room temperature for 30 min. The suspension was then concentrated and the resulting solid triturated with hexanes to afford the title compound (0.032 g, 86%) as an off-white solid: Rf0.38 (97.5:2.5 methylene chloride/methanol); mp 135-140° C.; 1H NMR (300 MHz, CD3OD) δ 8.60 (d, J=4.8 Hz, 2H), 7.50-7.00 (m, 10H), 6.65 (d, J=8.7 Hz, 1H), 6.44 (d, J=3.6 Hz, 1H), 6.36 (d, J=3.6 Hz, 1H), 5.86 (d, J=8.7 Hz, 1H), 5.16 (s, 2H); IR (ATR) 3303, 3086, 2714, 1662, 1628, 1567, 1484, 1401, 1300, 1211, 902, 855, 757 cm−1; ESI MS m/z 454 [C26H20ClN5O+H]+; HPLC (Method 1) 95.7% (AUC), tR=12.48 min. Anal. Calcd for C26H20ClN5O.HCl.1.25H2O: C, 60.88; H, 4.62; N, 13.65. Found: C, 61.12; H, 4.54; N, 13.31.

Workup

  1. concentrationThe suspension was then concentrated
  2. customthe resulting solid triturated with hexanes

Sources & evidence

ORD record
ord-657a288734a84f10ae90ffc5c91a311b
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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