Dimethylformamide dimethyl acetal → HCID 57890007, compound

HRID 1016141Notes

Reaction equation

HRID 1016141 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C@H:10]([CH:29]([CH3:31])[CH3:30])[C:11]([N:13]1[CH2:18][CH2:17][C@@:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)([OH:19])[C:15]([CH3:28])([CH3:27])[CH2:14]1)=[O:12])=[O:8])(=[O:3])[CH3:2].[CH3:35][N:36]([CH:38](OC)OC)[CH3:37]>>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C@@:16]2([OH:19])[CH2:17][CH2:18][N:13]([C:11](=[O:12])[C@H:10]([NH:9][C:7](=[O:8])[C:6]3[CH:32]=[CH:33][CH:34]=[C:4]([C:1](=[O:3])/[CH:2]=[CH:35]/[N:36]([CH3:38])[CH3:37])[CH:5]=3)[CH:29]([CH3:30])[CH3:31])[CH2:14][C:15]2([CH3:28])[CH3:27])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57889747HCID 57889747, compound

Product 1

HCID 57890007HCID 57890007, compound

Conditions

Temperature
105 °C

Procedure

3-Acetyl-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)benzamide was added DMF-DMA (0.3 mL) and the reaction mixture heated at 105° C. for ˜5 h. The residual DMF-DMA was removed on a rotovap and the crude product was dried on house high vac for ˜3 h to afford N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-((E)-3-(dimethylamino)acryloyl)benzamide.

Workup

  1. customThe residual DMF-DMA was removed on a rotovap
  2. dry with materialthe crude product was dried on house high vac for ˜3 h

Sources & evidence

ORD record
ord-b45106247f524cc7b4d5587d03b6ff87
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

Loading…