Isopropyl Acetate → HCID 58109343, compound

HRID 1046173Notes

Reaction equation

HRID 1046173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[C:38]1[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][N:39]=1.C(OC(C)C)(=O)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]2([CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:18]=[CH:19][C:20]([C:38]4[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][N:39]=4)=[CH:21][CH:22]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7915Isopropyl AcetateHCID 50057186-Bromopyridine-3-carbonitrileHCID 59635794HCID 59635794, compound

Product 1

HCID 58109343HCID 58109343, compound

Procedure

The title compound was prepared from (S)-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one and 2-bromo-5-cyanopyridine following procedures analogous to those described in Example 1 Step 2. LC-MS Method 2 tR=1.301, m/z=416; 1H NMR (CDCl3) 1.09 (d, 6H), 1.49 (d, 3H), 2.09-2.22 (m, 4H), 2.37 (m, 1H), 2.87 (m, 1H), 5.68 (m, 1H), 6.92-7.01 (t, 2H), 7.06 (m, 2H), 7.23 (m, 2H), 7.71 (d, 1H), 7.78 (d, 2H), 7.91 (d, 1H), 8.88 (s, 1H). The compound was dissolved in refluxing isopropyl acetate and allowed to cool slowly to afford a solid with mp 155-157° C.

Workup

  1. dissolutionThe compound was dissolved
  2. temperatureto cool slowly
  3. customto afford a solid with mp 155-157° C.

Sources & evidence

ORD record
ord-f50abb0517214f7cb62e4dd2f7c41c91
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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