Methylamine → HCID 69089225, compound

HRID 1930436Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[C:29](=[O:30])[N:28]([CH3:31])[C:21]4[N:22]=[C:23](SC)[N:24]=[CH:25][C:20]=4[CH:19]=3)[CH:15]=[CH:14][C:13]=2[F:32])=[O:10])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].[CH3:37][NH2:38].C1COCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[C:29](=[O:30])[N:28]([CH3:31])[C:21]4[N:22]=[C:23]([NH:38][CH3:37])[N:24]=[CH:25][C:20]=4[CH:19]=3)[CH:15]=[CH:14][C:13]=2[F:32])=[O:10])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69296329HCID 69296329, compound

Product 1

HCID 69089225HCID 69089225, compoundYield 67%

Procedure

Using a procedure analogous to Example A1, 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (55 mg, 0.100 mmol) and 2.00N methylamine in THF (4.00 mL, 8.0 mmol) were combined to provide 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (36 mg, 67% yield). 1H NMR (300 MHz, DMSO-d6): δ 2.90 (s, 3 H), 3.53-3.61 (m, 3 H), 7.26-7.31 (m, 2 H), 7.58-7.59 (m, 2 H), 7.60-7.75 (br. m, 1 H), 7.88 (s, 1 H), 8.10 (s, 1 H), 8.33-8.35 (m, 1 H), 8.64-8.77 (m, 2 H), 9.49 (s, 1H); MS (ESI) m/z: 521.0 (M+H+).

Sources & evidence

ORD record: ord-597f6bedf51a42e289d24f142862b948
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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