Isobutylene oxide → HCID 73055733, compound

HRID 1055466Notes

Reaction equation

HRID 1055466 reaction equation
[NH2:1][C@@H:2]([CH3:36])[C:3]([NH:5][C@H:6]1[CH2:12][O:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[N:8]([CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]#[N:34])[N:19]=2)[C:7]1=[O:35])=[O:4].[CH3:37][C:38]1([CH3:41])[CH2:40][O:39]1>CCO>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][N:8]2[C:7](=[O:35])[C@@H:6]([NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH2:37][C:38]([OH:39])([CH3:41])[CH3:40])[CH3:36])[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]2=3)=[N:19]1)#[N:34]

Participants

4

Reactant 2

HCID 11208Isobutylene oxide2×HCID 73055729HCID 73055729, compound

Product 1

HCID 73055733HCID 73055733, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(S)-2-Amino-N-((S)-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)propanamide (50 mg, 104 μmol, Eq: 1.00), LiClO4 (11.1 mg, 4.56 μl, 104 μmol, Eq: 1.00) and 2,2-dimethyloxirane (1 mL) were mixed with EtOH (7 mL) in a microwave reaction vial, the vial was sealed and heated in the microwave at 100° C. After 2 h, 20 eq of 2,2-dimethyloxirane were added and heating was continued under microwave at 100° C. for 3 h. The mixture was concentrated and the residue was purified by preparative TLC to give the title compound (34 mg, 59.1%) as a solid. MS m/z 553 (MH+)

Workup

  1. customthe vial was sealed
  2. temperatureheating
  3. waitwas continued under microwave at 100° C. for 3 h
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a48a3aab991848739343c209d58b5ef6
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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