Tetrahydrofuran → HCID 118093812, compound

HRID 1056938Notes

Reaction equation

NC1[C:3]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[F:39])=[C:4]([C:10]2[C:11]3[CH:20]=[CH:19][N:18]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[C:12]=3[C:13](=[O:17])[N:14]([CH3:16])[CH:15]=2)[CH:5]=[CH:6]C=1NC.C1N=CN([C:45]([N:47]2[CH:51]=[N:50][CH:49]=[CH:48]2)=O)C=1.[O:52]1CCCC1>>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[O:31][C:3]1[C:49]2[NH:50][C:51](=[O:52])[N:47]([CH3:45])[C:48]=2[CH:6]=[CH:5][C:4]=1[C:10]1[C:11]2[CH:20]=[CH:19][N:18]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:22])=[O:23])[C:12]=2[C:13](=[O:17])[N:14]([CH3:16])[CH:15]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 682631,1'-Carbonyldiimidazole

HCID 118093926HCID 118093926, compound

Product 1

HCID 118093812HCID 118093812, compoundYield 75%

Conditions

Temperature: 50 °C

Procedure

A solution of 4-[3-amino-2-(2,4-difluorophenoxy)-4-(methylamino)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (98.0 mg, 0.178 mmol) in tetrahydrofuran (1.0 mL) was treated with N,N-carbonyldiimidazole (57.7 mg, 0.356 mmol) and stirred at 50° C. for 1 h. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (77 mg, 75%). LCMS calculated for C29H23F2N4O5S (M+H)+: m/z=577.1. found: 577.1.

Workup

customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record: ord-b179011327174a018b2a486190d54e8e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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