Methylamine tetrahydrofuran → HCID 69096052, compound

HRID 1930472Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][C:5]([NH:22][C:23]([NH:25][C:26]2[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[O:28][N:27]=2)=[O:24])=[C:4]([F:34])[CH:3]=1.[CH3:35][NH2:36].C1COCC1>>[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13]([NH:36][CH3:35])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][C:5]([NH:22][C:23]([NH:25][C:26]2[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[O:28][N:27]=2)=[O:24])=[C:4]([F:34])[CH:3]=1

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69088987HCID 69088987, compound

Product 1

HCID 69096052HCID 69096052, compoundYield 48%

Procedure

Using a procedure analogous to Example A1, 1-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(5-isopropylisoxazol-3-yl)urea (0.113 g, 0.225 mmol) and 2.0M MeNH2/THF (1.12 ml, 2.25 mmol) were combined to afford 1-(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(5-isopropylisoxazol-3-yl)urea (52 mg, 48% yield) as a faintly yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.85 (s, 1H), 8.94 (brs, 1H), 8.62 (s, 1H), 8.15 (d, J=8.8 Hz, 1H), 7.88 (brq, J=4.8 Hz, 1H), 7.77 (s, 1H), 7.58 (d, J=10.8 Hz, 1H), 6.46 (s, 1H), 3.59 (s, 3H), 3.00 (septet, J=6.8 Hz, 1H), 2.91 (d, J=4.8 Hz, 3H), 1.20 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 486.2 (M+H+), 488.3 (M+2+H+).

Sources & evidence

ORD record: ord-dac52bed3cc14d909e869716967ab2e4
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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