Hexane → HCID 178455249, compound

HRID 2169365Notes

Reaction equation

HRID 2169365 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29](O)=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:32]([O:39][CH2:40][CH2:41][NH:42][CH2:43][CH:44]1[CH2:46][CH2:45]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[Si:32]([O:39][CH2:40][CH2:41][N:42]([CH2:43][CH:44]1[CH2:45][CH2:46]1)[C:29]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:30])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 8058HexaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69361897[2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amineHCID 178524871HCID 178524871, compound

Product 1

HCID 178455249HCID 178455249, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (324) (350 mg, 0.79 mmol) in dimethylformamide (7.5 mL) were added [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amine (8i) (274 mg, 1.19 mmol) N,N-diisopropylethylamine (0.4 mL), 2.39 mmol) and HATU (364 mg, 0.96 mmol). The reaction mixture was stirred at room temperature for 1 h while silica thin layer chromatography was performed (ethyl acetate:hexane=1:1/UV/SiO2, Rf=0.5). The reaction mixture was diluted with ethyl acetate (60 mL), washed with brine (3×30 mL) and dried and concentrated in vacuo to get a crude mass of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (329) (600 mg) which was used directly in the next step without further purification.

Workup

  1. washwashed with brine (3×30 mL)
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21ce6d2ae5704c6eabb826f169604dad
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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