L-Alaninol → HCID 69036147, compound

HRID 1930438Notes

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](SC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[O:30][N:29]=[C:28]([CH:31]([CH3:33])[CH3:32])[CH:27]=1)=[O:24].[NH2:34][C@H:35]([CH2:37][OH:38])[CH3:36]>>[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:34][C@@H:35]([CH3:36])[CH2:37][OH:38])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[O:30][N:29]=[C:28]([CH:31]([CH3:33])[CH3:32])[CH:27]=1)=[O:24]

Participants

Reactant 2

HCID 80307L-Alaninol

HCID 68982045HCID 68982045, compound

Product 1

HCID 69036147HCID 69036147, compoundYield 51%

Procedure

Using a procedure analogous to Example A1, 1-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-isopropylisoxazol-5-yl)urea (0.150 g, 0.322 mmol, 1.00 eq) was oxidized and reacted with L-alaninol (41.4 μL, 0.533 mmol, 2.00 eq) to afford (S)-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-isopropylisoxazol-5-yl)urea (67 mg, 51% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.34 (s, 1H), 8.73 (brs, 1H), 8.65 (brs, 1H), 8.39 (dd, J=2.4 and 8.0 Hz, 1H), 7.87 (s, 1H), 7.60-7.57 (m, 1H), 7.35-7.25 (m, 2H), 6.06 (s, 1H), 4.70 (t, J=6.0 Hz, 1H), 4.09 (brs, 1H), 3.58-3.49 (m, 4H), 3.35 (brs, 1H), 2.89 (m, 1H), 1.23 (s, 9H), 1.17-1.15 (m, 9H); MS (ESI) m/z: 496.3 (M+H+).

Sources & evidence

ORD record: ord-d7a47c20bdcc40e5810874b0bbde1cbe
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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