Diethyl Ether → HCID 10119565, compound

HRID 970936Notes

Reaction equation

HRID 970936 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[C:11]2[CH2:19][N:20]([CH2:31][C:32]2[CH:48]=[CH:47][C:35]([CH2:36][NH:37][S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[CH:21]2[C:30]3[N:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:24][CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.C(OCC)C>Br.CC(O)=O>[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][N:20]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:36][NH:37][S:38]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)(=[O:40])=[O:39])=[CH:47][CH:48]=1)[CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 10305305HCID 10305305, compound

Product 1

HCID 10119565HCID 10119565, compound

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of N-(4-{[(1-benzenesulfonyl-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-benzenesulfonamide (AMD9830) (161 mg, 0.234 mmol) in saturated HBr/AcOH (3 mL) was stirred at room temperature for 3.5 h, then diethyl ether (20 mL) was added to give a colourless precipitate. The supernatant was decanted, and the residue was partitioned between CH2Cl2 (10 mL) and saturated NaHCO3(aq) (15 mL). The basic aqueous phase was extracted with CH2Cl2 (10 mL), and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH) gave AMD9845 (59 mg, 44%) as a yellow foam. 1H NMR (CDCl3) δ 1.68 (m, 1H), 1.99 (m, 2H), 2.24 (m, 1H), 2.67-2.91 (m, 2H), 3.68 (s, 2H), 3.86 (d, 1H, J=17 Hz), 4.05 (m, 3H), 4.14 (d, 1H, J=17 Hz), 4.87 (m, 1H), 7.01 (d, 2H, J=7.8 Hz), 7.18 (m, 3H), 7.28 (m, 2H), 7.37-7.60 (m, 6H), 7.80 (m, 2H), 8.68 (m, 1H); 13C NMR (CDCl3) δ 22.08, 24.18, 29.90, 47.66, 49.21, 54.47, 61.26, 122.30, 123.03, 127.75, 128.54, 129.65, 129.73, 133.29, 135.47, 135.74, 138.01, 139.87, 140.65, 147.63, 156.87, 158.03. ES-MS m/z 538 (M+H). Anal. Calcd. for C31H31N5SO2.0.46CH2Cl2: C, 65.52; H, 5.58; N, 12.14. Found: C, 65.56; H, 5.60; N, 12.09.

Workup

  1. customto give a colourless precipitate
  2. customThe supernatant was decanted
  3. customthe residue was partitioned between CH2Cl2 (10 mL) and saturated NaHCO3(aq) (15 mL)
  4. extractionThe basic aqueous phase was extracted with CH2Cl2 (10 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH)
  9. customgave AMD9845 (59 mg, 44%) as a yellow foam

Sources & evidence

ORD record
ord-d03102ec100a4cfe82e18c83b8a0ad39
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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