HCID 10006107, compound → HCID 10006108, compound

HRID 1294736Notes

Reaction equation

HRID 1294736 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:34])[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:19]=2)[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].NC1C=C(C(C2C=CC(C(N(CC)CC)=O)=CC=2)N2CCN(C(OC(C)(C)C)=O)CC2)C=CC=1>>[CH2:36]([N:3]([CH2:1][CH3:2])[C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:34])[CH2:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:19]=2)[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:37]

Participants

3

Reactant 2

HCID 10006107HCID 10006107, compoundHCID 11590834HCID 11590834, compound

Product 1

HCID 10006108HCID 10006108, compound

Procedure

Synthesized according to the method used for COMPOUND 41 except that INTERMEDIATE 5a was used. The residue was purified by flash chromatography, eluting 25% methanol in dichloromethane, rising to 40% methanol in dichloromethane. The product was converted to the hydrochloride salt using 2M HCl in diethyl ether to give COMPOUND 65 as a colourless solid. Purity (HPLC): >99%; Optical purity (Chiral HPLC): >99%; 1H NMR (400 MHz, CD3OD) 1.06 (t, J=6.64 Hz, 3H), 1.19 (t, J=6.88 Hz, 3H), 2.61 (t, J=7.66 Hz, 2H), 2.56-2.67 (m, 4H), 2.95 (t, J=7.66 Hz, 2H), 3.18-3.26 (m, 6H), 3.45-3.53 (m, 2H), 4.41 (s, 1H), 7.13-7.16 (m, 2H), 7.19-7.24 (m, 6H), 7.30 (d, J=8.30 Hz, 2H), 7.52 (d, J=8.20 Hz, 2H), Found: C, 61.14; H, 6.86; N, 9.10. C31H38N4O2×2.9HCl×0.3H2O has C, 61.06; H, 6.86; N, 9.19%. [a]D20=−0.96 deg [c 0.73, MeOH].

Workup

  1. customSynthesized
  2. customThe residue was purified by flash chromatography
  3. washeluting 25% methanol in dichloromethane

Sources & evidence

ORD record
ord-6e7e2fe506cb4984bb6f18ec188b55fa
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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