Methanol → HCID 67256841, compound

HRID 1509285Notes

Reaction equation

HRID 1509285 reaction equation
[C:1]([C:4]1[N:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:14]([C:23]4[CH:28]=[CH:27][C:26]([C:29]5([NH:33]C(=O)OC(C)(C)C)[CH2:32][CH2:31][CH2:30]5)=[CH:25][CH:24]=4)=[N:13][C:10]=3[O:11][CH2:12][C:7]2=[N:6][N:5]=1)(=[O:3])[NH2:2].CO>ClCCl>[NH2:33][C:29]1([C:26]2[CH:27]=[CH:28][C:23]([C:14]3[C:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:16][C:9]4[N:8]5[C:4]([C:1]([NH2:2])=[O:3])=[N:5][N:6]=[C:7]5[CH2:12][O:11][C:10]=4[N:13]=3)=[CH:24][CH:25]=2)[CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 887MethanolHCID 86683655HCID 86683655, compound

Product 1

HCID 67256841HCID 67256841, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl (1-(4-(1-carbamoyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.019 mmol) was dissolved in dichloromethane (0.5 ml); this solution was added to a scx-2 catch and release cartridge (1 g), precalibrated using methanol (15 ml) and dichloromethane (15 ml). After allowing to binding for 15 hours, the column was washed with methanol (6 ml) and then the product eluted with 7M ammonia in methanol (4 ml×2). The combined product fractions were concentrated to dryness under reduced pressure to give the desired product as a white solid (5 mg, 61% yield). LCMS (Method D) RT=0.695 min, M+1=440. 1H-NMR (500 MHz, CD3OD) δ 8.80 (1H, s), 7.27-7.24 (4H, bs), 7.22-7.17 (3H, m), 7.16-7.13 (2H, m), 5.57 (2H, s), 2.49-2.38 (2H, m), 2.19-2.10 (2H, m), 2.03-1.92 (1H, m), 1.71-1.60 (1H, m).

Workup

  1. additionthis solution was added to a scx-2 catch and release cartridge (1 g)
  2. washthe column was washed with methanol (6 ml)
  3. washthe product eluted with 7M ammonia in methanol (4 ml×2)
  4. concentrationThe combined product fractions were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-235aa624f25844a6b6f1d61d0ae3860a
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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