Trifluoroacetic acid → HCID 90284612, compound

HRID 519146Notes

Reaction equation

HRID 519146 reaction equation
C(OC([N:8]1[CH2:11][C:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2/[CH:28]=[CH:29]/OCC)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:34])[C:19](=[O:33])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.BrC1C(NC2(C)CN(C(OC(C)(C)C)=O)C2)=CC2N3C(C)C(=O)NN=C3COC=2C=1.C([SiH](CC)CC)C.[C:72]([OH:78])([C:74]([F:77])([F:76])[F:75])=[O:73]>>[F:75][C:74]([F:77])([F:76])[C:72]([OH:78])=[O:73].[CH3:34][CH:18]1[N:17]2[C:16]3[CH:15]=[C:14]4[C:27]([CH2:28][CH2:29][N:13]4[C:10]4([CH3:12])[CH2:11][NH:8][CH2:9]4)=[CH:26][C:25]=3[O:24][CH2:23][C:22]2=[N:21][NH:20][C:19]1=[O:33]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 90220758HCID 90220758, compoundHCID 90220768HCID 90220768, compound

Product 1

HCID 90284612HCID 90284612, compound

Procedure

A mixture of 3-[7-((E)-2-ethoxy-vinyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl 3-((8-bromo-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)-3-methylazetidine-1-carboxylate (Preparation #18) using the similar procedure detailed in Example #148, Step H) 0.65 g, 1.378 mmol) in TFA (4 mL) was stirred at ambient temperature for 20 min. Triethylsilane (4.8 g, 41.4 mmol) was added and the reaction mixture was stirred for 24 h. The solvent was removed in vacuo to give 1-methyl-10-(3-methylazetidin-3-yl)-5,8,9,10-tetrahydro-1H-[1,2,4]triazino[4′,3′:4,5][1,4]oxazino[2,3-f]indol-2(3H)-one 2,2,2-trifluoroacetate (0.65 g, crude). Prep-HPLC (Table 3, Method 29) purification of 20 mg of crude product gave 1-methyl-10-(3-methyl-azetidin-3-yl)-3,5,9,10-tetrahydro-8H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one 2,2,2-trifluoroacetate (0.011 g). 1H NMR (400 MHz, DMSO-d6): δ 10.69 (s, 1H), 9.15 (s, 1H), 8.91 (brs, 1H), 6.80 (s, 1H), 5.95 (s, 1H), 4.98 (m, 1H), 4.45 (s, 2H), 4.11 (m, 4H), 3.25 (m, 1H), 2.84 (m, 2H), 1.40 (s, 3H), 1.20 (m, 3H). LC/MS (Table 1, Method 4) Rt=0.799 min; MS m/z: 328 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred for 24 h
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-10afed55f8a443489df9669c01e8b850
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…