2-Amino-2-phenylpropan-1-ol → (Rs)-4-(4-aminophenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-n-(1-hydroxy-2-phenylpropan-2-yl)benzamide

HRID 605432Notes

Reaction equation

HRID 605432 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=2[NH:18][C:19]2[C:20]3[CH:28]=[C:27]([F:29])[C:26]([CH:30]([CH3:32])[CH3:31])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[CH:4][CH:3]=1.[NH2:33][C:34]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH3:37])[CH2:35][OH:36]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:33][C:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([CH3:37])[CH2:35][OH:36])=[O:14])=[CH:11][C:10]=2[NH:18][C:19]2[C:20]3[CH:28]=[C:27]([F:29])[C:26]([CH:30]([CH3:31])[CH3:32])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3497332-Amino-2-phenylpropan-1-olHCID 670407504-(4-Aminophenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzoic acid

Product 1

HCID 67041180(Rs)-4-(4-aminophenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-n-(1-hydroxy-2-phenylpropan-2-yl)benzamideYield 30%

Procedure

The title compound was prepared (yield 30%) by the procedure of Example 449I, substituting the product of Example 451D for the product of Example 449H. 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=7.0 Hz, 6H), 1.69 (s, 3H), 3.43-3.58 (m, 2H), 3.74 (dd, J=10.7, 5.9 Hz, 1H), 5.09 (t, J=5.9 Hz, 1H), 5.57 (br-s, 2H), 6.62 (d, J=8.5 Hz, 2H), 6.86 (d, J=8.5 Hz, 1H), 7.12 (d, J=8.5 Hz, 2H), 7.17 (br-t, J=7.0 Hz, 1H), 7.27 (t, J=7.0 Hz, 2H), 7.33 (br-d, J=7.0 Hz, 2H), 7.68 (dd, J=8.5, 1.5 Hz, 1H), 7.83 (d, J=1.5 Hz, 1H), 8.04 (s, 1H), 8.60 (s, 1H), 8.76 (d, J=10.3 Hz, 1H), 10.10 (s, 1H). MS ESI+ m/z: 583 (M+H), ESI− m/z: 581 (M−H).

Sources & evidence

ORD record
ord-6aadd6dcdd2b424886900b8248937996
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…