Water → HCID 68157785, compound

HRID 243165Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylamine (518 μl, 3.72 mol) was added to (S)-2-amino-N-[4-fluoro-2-(pyrimidin-2-ylamino)phenyl]propionamide hydrochloride salt 161b (289 mg, 0.93 mmol) and 6-chloro-9-(tetrahydropyran-2-yl)purine (265 mg, 1.10 mol) in IPA (5.0 ml) and heated to 80° C. overnight. The reaction was poured into water and the aqueous layer extracted into EtOAc (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% 2M ammonia methanol/DCM) to yield the title compound as a 1:1 mixture of diastereomers (236 mg, 0.50 mmol, 53%). LCMS RT 2.63 min [M+H]+ 478.2.

Workup

extractionthe aqueous layer extracted into EtOAc (×3)
washThe combined organic fractions were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe product was purified by chromatography (SiO2, 0-10% 2M ammonia methanol/DCM)

Sources & evidence

ORD record: ord-b36338409311434ab698752a455f00e9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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