2-Aminopropanol → HCID 69298115, compound

HRID 1930441Notes

Reaction equation

HRID 1930441 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13](NC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)=[O:24].[NH2:36][CH:37]([CH3:40])[CH2:38][OH:39]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13]([NH:36][CH:37]([CH3:40])[CH2:38][OH:39])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=1)=[O:24]

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 69296195HCID 69296195, compound

Product 1

HCID 69298115HCID 69298115, compoundYield 921.8%

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 from Example 67 (55 mg, 0.100 mmol) and 2-amino-1-propanol (249 mg, 3.31 mmol) were combined to provide 1-(2-fluoro-5-(2-(1-hydroxypropan-2-ylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (489 mg, 22% yield). 1H NMR (300 MHz, DMSO-d4), δ 1.15 (s, 3H), 3.37-3.56 (m, 4 H), 3.90-4.15 (m, 1 H), 4.69 (s, 1 H), 7.22-7.55 (m, 6 H), 7.84 (s, 1 H), 8.02 (s, 1 H), 8.36-8.38 (m, 1 H), 8.63 (br. s, 2 H), 9.38 (s, 1 H), OH missing; MS (ESI) m/z: 531.2 (M+H+).

Sources & evidence

ORD record
ord-20a7ec8a050a42b38cb8792b2b971c4c
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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