Methanol → HCID 69038230, compound

HRID 1930489Notes

Reaction equation

HRID 1930489 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C([C:43](OO)=[O:44])C=1.CO.C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([O:44][CH3:43])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 69297975HCID 69297975, compound

Product 1

HCID 69038230HCID 69038230, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-(3-tert-butylisoxazol-5-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 96 (15 mg, 0.030 mmol) in CH2Cl2 (1 mL) was treated with mCPBA (70%, 8.94 mg, 0.036 mmol). After 30 min, methanol (0.050 mL 1.2 mmol) and triethylamine (0.020 mL, 0.14 mmol) were added and the resultant mixture was heated to 40° C. overnight. The reaction was concentrated in vacuo and purified by chromatography to provide 1-(3-tert-butylisoxazol-5-yl)-3-(2-fluoro-5-(2-methoxy-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-4-methylphenyl)urea. (8.6 mg, 59% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.32 (s, 1H), 8.93 (s, 1H), 8.72 (s, 1H), 7.93 (d, J=8.3 Hz, 1H), 7.90 (s, 1H), 7.20 (d, J=12.3 Hz, 1H), 6.00 (s, 1H), 4.02 (s, 3H), 3.63 (s, 3H), 2.09 (s, 3H), 1.21 (s, 9H); MS (ESI) m/z: 481.2 (M+H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by chromatography

Sources & evidence

ORD record
ord-22a1a8e555044a85b7cf7d95525e53af
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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