Methanol → HCID 53261683, compound

HRID 1509296Notes

Reaction equation

HRID 1509296 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[C:11]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)=[CH:12][C:3]1=2.CO>ClCCl>[NH2:28][C:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:10]3[C:11]([C:13]4[CH:17]=[CH:16][S:15][CH:14]=4)=[CH:12][C:3]4[N:2]([CH3:1])[C:7](=[O:8])[CH2:6][O:5][C:4]=4[N:9]=3)=[CH:19][CH:20]=2)[CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 887MethanolHCID 86683663HCID 86683663, compound

Product 1

HCID 53261683HCID 53261683, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl (1-(4-(1-methyl-2-oxo-7-(thiophen-3-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (25 mg, 0.051 mmol) was dissolved in dichloromethane (0.5 ml); this solution was added to a scx-2 catch and release cartridge (5 g), precalibrated using methanol (15 ml) and dichloromethane (15 ml). After allowing binding for 12 hours, the column was washed with methanol (6 ml), then the product eluted with 7M ammonia in methanol (4×2 ml). The combined product fractions were concentrated to dryness under reduced pressure to give the desired product as a white solid (5.8 mg, 30% yield). LCMS (Method D): RT=0.777 min, M+1=393. 1H-NMR (500 MHz, CD3OD) δ 7.35-7.29 (3H, m), 7.28-7.25 (1H, dd), 7.21-7.18 (1H, s), 7.17-7.14 (1H, dd), 7.07-7.03 (1H, dd), 6.71-6.67 (1H, dd), 4.80 (2H, s), 3.32 (3H, s), 2.51-2.37 (4H, m), 2.25-2.13 (1H, m).

Workup

  1. additionthis solution was added to a scx-2 catch and release cartridge (5 g)
  2. washthe column was washed with methanol (6 ml)
  3. washthe product eluted with 7M ammonia in methanol (4×2 ml)
  4. concentrationThe combined product fractions were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1f6f4a842e144cb5a0cb8a234e13f844
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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