Hydrochloric Acid → HCID 90409126, compound

HRID 589122Notes

Reaction equation

HRID 589122 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][C@H:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[N:12]4[C:23]([N:25]5[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)=[N:24][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:39])[O:4][N:3]=1.Cl>O1CCOCC1>[N:25]1([C:23]2[N:12]3[C@@H:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:14][O:15][C:16]4=[C:11]3[C:10](=[CH:9][CH:8]=[C:7]4[C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:39])[N:24]=2)[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86299232HCID 86299232, compound

Product 1

HCID 90409126HCID 90409126, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-[(4S)-7-(3,5-dimethylisoxazol-4-yl)-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2-yl]-1,4-diazepane-1-carboxylate (53 mg, 0.10 mmol) was treated with a solution of 4.0 M hydrogen chloride in 1,4-dioxane (2.0 mL) for 10 min. The mixture was concentrated and purified by preparative LCMS using pH 10 buffer to give the title compound (28.5 mg, 66%). LCMS calc. for C24H27N6O2 (M+H)+: m/z=431.2. found: 431.3.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-2dd7c6c0f6ad4b47b3d36efbe5450a76
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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