Ethanol → HCID 22291741, compound

HRID 968107Notes

Reaction equation

HRID 968107 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([N:16]3[C:24]4[C:23]5[CH:25]=[C:26]([NH:29][C:30]([C:32]6[C:37]([Cl:38])=[CH:36][CH:35]=[C:34](Cl)[N:33]=6)=[O:31])[CH:27]=[CH:28][C:22]=5[CH2:21][CH2:20][C:19]=4[C:18]([C:40]([NH2:42])=[O:41])=[N:17]3)=[CH:15][C:10]=2[O:9][CH2:8]1.CCO>CC(N(C)C)=O>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([N:16]3[C:24]4[C:23]5[CH:25]=[C:26]([NH:29][C:30]([C:32]6[C:37]([Cl:38])=[CH:36][CH:35]=[C:34]([N:1]7[CH2:6][CH2:5][O:4][CH2:3][CH2:2]7)[N:33]=6)=[O:31])[CH:27]=[CH:28][C:22]=5[CH2:21][CH2:20][C:19]=4[C:18]([C:40]([NH2:42])=[O:41])=[N:17]3)=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8083MorpholineHCID 22291830HCID 22291830, compound

Product 1

HCID 22291741HCID 22291741, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was synthesized from 0.27 g of morpholine and the title compound of Example 216 (0.522 g) by the same procedure used for Example 207 except that EtOH was replaced by 0.5 ml of DMA. The reaction was carried out at 80° C. for 36 hours. The title compound, isolated by preparative HPLC, is a white solid (0.30 g, 52%), m.p. 260-262° C. (decomposition). Its structure was confirmed by 1H NMR and LC/MS: 1H NMR (CDCl3) δ 2.96 (m, 2H), 3.15 (m, 2H)), 3.48 (m, 4H), 3.86 (m, 4H), 5.41 (s, 1H), 6.74-6.86 (m, 2H), 6.90-7.04 (m, 2H), 7.16 (d, 1H, J=1 Hz), 7.28-7.35 (m, 2H), 7.54-7.22 (m, 2H), 9.32 (s, 1H). ESI mass spectrum for C29H26ClN6O5+: 573 (M+1).

Sources & evidence

ORD record
ord-67c34aafa1b24616b23c01e7f22f141b
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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