Triethylamine → (R)-((R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxy-2-methylbut-3-ynyl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

HRID 1984118Notes

Reaction equation

HRID 1984118 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:29])[C:5]2[C:10]([C:11]#[C:12][C@@:13]([CH3:17])([OH:16])[CH2:14][OH:15])=[CH:9][N:8]([CH2:18][C:19]3[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=3)[C:6]=2[N:7]=1.[CH3:30][O:31][C@@:32]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:36]([F:39])([F:38])[F:37])[C:33](Cl)=[O:34].CCN(CC)CC.CCOC(C)=O.C(Cl)Cl>C1COCC1>[F:37][C:36]([F:38])([F:39])[C@@:32]([O:31][CH3:30])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:33]([O:15][CH2:14][C@@:13]([OH:16])([CH3:17])[C:12]#[C:11][C:10]1[C:5]2[C:4]([Cl:29])=[N:3][C:2]([NH2:1])=[N:7][C:6]=2[N:8]([CH2:18][C:19]2[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=2)[CH:9]=1)=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724611alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, (S)-(+)-HCID 21226138Dichloromethane ethylacetateHCID 57713869(R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol

Product 1

HCID 57713830(R)-((R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxy-2-methylbut-3-ynyl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol (see example 53) (22 mg), (S)-(+)-α-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride (45 μL), and Et3N (50 μL) in THF (3.0 mL) was heated to 40° C. overnight. Preparative TLC (EtOAc/DCM 25:65) gave the title compound, as a solid. HPLC Rt=6.44 min.

Sources & evidence

ORD record
ord-0ddf616acc2948c189239592214e4490
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

Loading…