4-chloro-N-{4-[(2-oxido-1,3,2-dioxaphosphinan-2-yl)methyl]phenyl}-5-(trifluoromethyl)pyrimidin-2-amine → HCID 178479964, compound

HRID 511468Notes

Reaction equation

HRID 511468 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][P:20]3(=[O:26])[O:25][CH2:24][CH2:23][CH2:22][O:21]3)=[CH:15][CH:14]=2)[N:3]=1.[NH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH:39]2[CH2:44][CH2:43][CH:42]([OH:45])[CH2:41][CH2:40]2)=[C:32]2[C:36]=1[C:35](=[O:37])[N:34]([CH3:38])[CH2:33]2>>[OH:45][C@H:42]1[CH2:41][CH2:40][C@H:39]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][C:2]3[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([CH2:19][P:20]5(=[O:26])[O:25][CH2:24][CH2:23][CH2:22][O:21]5)=[CH:15][CH:14]=4)[N:3]=3)=[C:36]3[C:32]=2[CH2:33][N:34]([CH3:38])[C:35]3=[O:37])[CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 582929154-chloro-N-{4-[(2-oxido-1,3,2-dioxaphosphinan-2-yl)methyl]phenyl}-5-(trifluoromethyl)pyrimidin-2-amine2×HCID 672549257-amino-4-(4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 178479964HCID 178479964, compound

Procedure

The title compounds were prepared according to the procedure for compound 102 using 4-chloro-N-{4-[(2-oxido-1,3,2-dioxaphosphinan-2-yl)methyl]phenyl}-5-(trifluoromethyl)pyrimidin-2-amine (Compound 230A, 22.8 mg, 0.0559 mmol) and 7-amino-4-(4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (22.0 mg, 0.0845 mmol). The crude material was purified using a Teledyne/ISCO Combiflash system, eluting with 0-15% 7N NH3(MeOH):EtOAc. The collected material was a mixture of regioisomers and was purified again by Supercritical Fluid Chromatography (SFC).

Workup

  1. customThe crude material was purified
  2. washeluting with 0-15% 7N NH3(MeOH)
  3. additiona mixture of regioisomers
  4. customwas purified again by Supercritical Fluid Chromatography (SFC)

Sources & evidence

ORD record
ord-360a0c714d174d1d8c9564832d02ca4d
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…