HCID 81719713, compound → HCID 90313737, compound

HRID 1523876Notes

Reaction equation

HRID 1523876 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:34][C@@H:35]([CH3:43])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31]([NH:34][C@H:35]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH3:43])(=[O:32])=[O:33])=[CH:7][C:2]=2[F:1])=[CH:18][N:19]=1

Participants

3

Reactant 2

HCID 81719713HCID 81719713, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90313737HCID 90313737, compound

Procedure

The title compound was prepared using analogous conditions to those described in Example 571 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrimidin-2-amine and (S)-tert-butyl 2-(2-bromophenylsulfonamido)propanoate. MS (ESI): mass calcd. for C23H25FN4O4S, 472.16; m/z found, 473.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.65 (d, J=1.1, 2H), 8.08 (dd, J=8.0, 1.2, 1H), 7.66 (m, 1H), 7.61-7.49 (m, 2H), 7.37 (m, 3H), 3.66 (q, J=107.2, 1H), 1.34 (s, 9H), 1.26 (d, J=7.2, 3H).

Sources & evidence

ORD record
ord-58c77c9bdaca4400b5b2432f58a5b773
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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